phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Base Information

Chemical Name:phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside
CAS No.:124595-23-9
Molecular Formula:C₂₄H₃₆O₈SSi
Molecular Weight:512.697
Hs Code.:

Synonyms:phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

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Chemical Property of phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

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Technology Process of phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

There total 7 articles about phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

: 108-24-7
acetic anhydride

: phenyl 6-O-(tert-butyldimethylsilyl)-1-thio-β-D-glucopyranoside

: 124595-23-9
phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: With pyridine; at 0 - 20 ℃; for 5h;
DOI:10.1016/j.ejmech.2017.11.040

Reference yield:

: 108-24-7
acetic anhydride

: 18162-48-6
tert-butyldimethylsilyl chloride

: 13992-16-0,23661-28-1,24404-53-3,28512-68-7,65236-85-3,86782-39-0,108032-93-5,121524-01-4,121570-34-1
(2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate

: 124595-23-9
phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: (2R,3R,4S,5R,6S)-2-(acetoxymethyl)-6-(phenylthio)tetrahydro-2H-pyran-3,4,5-triyl triacetate; With sodium methylate; In methanol; at 20 ℃; for 2h;

tert-butyldimethylsilyl chloride; With 1H-imidazole; In N,N-dimethyl-formamide; at 0 ℃; for 12h;

acetic anhydride; With dmap; triethylamine; In dichloromethane; for 16h;
DOI:10.1021/acs.joc.0c01927

Reference yield:

: 83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5
D-glucose pentaacetate

: 124595-23-9
phenyl 2,3,4-tri-O-acetyl-6-O-tert-butyldimethylsilyl-1-thio-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / 12 h / 0 °C

2.1: sodium methylate / methanol / 2 h / 20 °C

2.2: 12 h / 0 °C

2.3: 16 h

With boron trifluoride diethyl etherate; sodium methylate; In methanol; dichloromethane;
DOI:10.1021/acs.joc.0c01927