Synthesis of glucosamine vinyl ether derivative and its deuterated analog

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Synthesis of glucosamine vinyl ether derivative and its deuterated analog. / Rodygin, K. S. ; Voronin, V. V. ; Ledovskaya , M. S. .

In: Russian Chemical Bulletin, Vol. 69, No. 7, 01.07.2020, p. 1401-1404.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{f9b96a563b2741b6b8b320c212b552ed,

title = "Synthesis of glucosamine vinyl ether derivative and its deuterated analog",

abstract = "The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.",

keywords = "calcium carbide, vinyl ether, glucosamine, deuterium labeling, vinylation",

author = "Rodygin, {K. S.} and Voronin, {V. V.} and Ledovskaya, {M. S.}",

note = "Rodygin, K.S., Voronin, V.V. & Ledovskaya, M.S. Synthesis of glucosamine vinyl ether derivative and its deuterated analog. Russ Chem Bull 69, 1401–1404 (2020). https://doi.org/10.1007/s11172-020-2915-3",

year = "2020",

month = jul,

day = "1",

doi = "10.1007/s11172-020-2915-3",

language = "English",

volume = "69",

pages = "1401--1404",

journal = "Russian Chemical Bulletin",

issn = "1066-5285",

publisher = "Springer Nature",

number = "7",

}

RIS

TY - JOUR

T1 - Synthesis of glucosamine vinyl ether derivative and its deuterated analog

AU - Rodygin, K. S.

AU - Voronin, V. V.

AU - Ledovskaya , M. S.

N1 - Rodygin, K.S., Voronin, V.V. & Ledovskaya, M.S. Synthesis of glucosamine vinyl ether derivative and its deuterated analog. Russ Chem Bull 69, 1401–1404 (2020). https://doi.org/10.1007/s11172-020-2915-3

PY - 2020/7/1

Y1 - 2020/7/1

N2 - The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.

AB - The use of calcium carbide (in the presence of H2O) as a source of acetylene in the reaction with methyl 2-amino-4,6-O-benzylidene-2-deoxy-β-D-glucopyranoside under superbasic conditions (KF, KOH, DMSO, 130 °C, 3 h) led to the corresponding vinyl ether in 78% yield. The vinylation does not affect other reaction centers. Replacement of water with deuterium oxide in the reaction mixture gave a stable deuterated analog of this vinyl ether in 72% yield. The one-step isotopic enrichment was practically quantitative (isotopic purity >96%). Introduced deuterium atoms can be used as a convenient label in further transformations.

KW - calcium carbide

KW - vinyl ether

KW - glucosamine

KW - deuterium labeling

KW - vinylation

UR - https://link.springer.com/article/10.1007/s11172-020-2915-3

UR - http://www.scopus.com/inward/record.url?scp=85090085904&partnerID=8YFLogxK

U2 - 10.1007/s11172-020-2915-3

DO - 10.1007/s11172-020-2915-3

M3 - Article

VL - 69

SP - 1401

EP - 1404

JO - Russian Chemical Bulletin

JF - Russian Chemical Bulletin

SN - 1066-5285

IS - 7

ER -

ID: 61434388