ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside

Base Information

• Chemical Name: ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 142270-28-8
• Molecular Formula: C₄₃H₅₄O₇SSi
• Molecular Weight: 743.049
• Mol file: 142270-28-8.mol

Synonyms:ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside

Chemical Property of ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside

There total 10 articles about ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside 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: 91.0%

C36H50O6SSi + benzoic acid (65-85-0,8013-63-6) → ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-28-8)

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/jacs.7b09461

Reference yield:

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (122588-51-6) → ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-28-8)

Guidance literature:

Multi-step reaction with 5 steps

1: 90 percent / 4-dimethylaminopyridine / pyridine / 2 h / Ambient temperature

2: conc. H₂SO₄ / acetic acid / 0.17 h

3: 78 percent / ZnCl₂ / CH₂Cl₂ / 3 h

4: 92 percent / 1M NaOMe / methanol / 2 h

5: 1) pyridine, 2) 4-dimethylaminopyridine / 1) r.t., overnight, 2) 30 min

With pyridine; dmap; sulfuric acid; sodium methylate; zinc(II) chloride; In pyridine; methanol; dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(00)90553-6

Reference yield:

methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside (142270-21-1) → ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-28-8)

Guidance literature:

Multi-step reaction with 4 steps

1: conc. H₂SO₄ / acetic acid / 0.17 h

2: 78 percent / ZnCl₂ / CH₂Cl₂ / 3 h

3: 92 percent / 1M NaOMe / methanol / 2 h

4: 1) pyridine, 2) 4-dimethylaminopyridine / 1) r.t., overnight, 2) 30 min

With pyridine; dmap; sulfuric acid; sodium methylate; zinc(II) chloride; In methanol; dichloromethane; acetic acid;

DOI:10.1016/S0008-6215(00)90553-6

upstream raw materials:

benzoyl chloride

tert-butyldimethylsilyl chloride

ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside

Downstream raw materials:

2-(4-trifluoroacetamidophenyl)ethyl O-(6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-tert-butyldimethylsilyl-L-glycero-α-D-manno-heptopyranosyl)-(1<*>3)-2,4,6,7-tetra-O-acetyl-L-glycero-α-D-manno-heptopyranoside

2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside

2-(4-trifluoroacetamidophenyl)ethyl O-<6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-L-glycero-α-D-manno-heptopyranosyl>-(1-3)-2,6,7-tri-O-acetyl-4-O-chloroacetyl-L-glycero-α-D-manno-heptopyranoside