phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside

Base Information

• Chemical Name: phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside
• CAS No.: 947256-84-0
• Molecular Formula: C₃₇H₆₄O₅SSi₃
• Molecular Weight: 705.235

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

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

Chemical Property:

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

There total 1 articles about phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-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: 83.0%

phenyl 6-O-benzyl-1-thio-α-D-glucopyranoside + t-butyldimethylsiyl triflate (69739-34-0) → phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside (947256-84-0)

Guidance literature:

With pyridine; dmap; at 60 ℃; for 24h;

DOI:10.1021/ja071955l

Reference yield: 63.0%

phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside (947256-84-0) + (2R,3R,4S,5R,6S)-4,5-Bis-benzyloxy-2-benzyloxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol (97974-20-4) → phenyl 2,3,6-tri-O-benzyl-4-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (947256-97-5)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -85 ℃; for 1h;

DOI:10.1021/ja071955l

Reference yield:

phenyl 6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-1-thio-α-D-glucopyranoside (947256-84-0) + phenyl 2,3,4-tri-O-benzyl-1-thio-β-D-glucopyranoside (87470-73-3,120403-26-1,38184-12-2) → phenyl 2,3,4-tri-O-benzyl-6-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-α-D-glucopyranosyl)-1-thio-β-D-glucopyranoside + phenyl 2,3,4-tri-O-benzyl-6-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside (947256-95-3)

Guidance literature:

With N-iodo-succinimide; trifluorormethanesulfonic acid; In dichloromethane; at -85 ℃; for 1h;

DOI:10.1021/ja071955l

upstream raw materials:

t-butyldimethylsiyl triflate

Downstream raw materials:

phenyl 2,3,4-tri-O-benzyl-6-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

phenyl 2,3,6-tri-O-benzyl-4-O-(6-O-benzyl-2,3,4-tri-O-tert-butyldimethylsilyl-β-D-glucopyranosyl)-1-thio-β-D-glucopyranoside

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