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

Base Information

• Chemical Name: ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside
• CAS No.: 142270-27-7
• Molecular Formula: C₃₀H₃₆O₆S
• Molecular Weight: 524.678
• Mol file: 142270-27-7.mol

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

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

There total 6 articles about ethyl 2,3,4-tri-O-benzyl-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: 92.0%

ethyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-23-3) → ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-27-7)

Guidance literature:

With sodium methylate; In methanol; for 2h;

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

Reference yield: 9.0%

(2R,3S,4S,5R,6R)-3,4,5-Tris-benzyloxy-2-ethylsulfanyl-6-vinyl-tetrahydro-pyran → ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-27-7) + ethyl 2,3,4-tri-O-benzyl-D-glycero-α-D-thio-manno-heptopyranoside

Guidance literature:

With potassium dioxotetrahydroxoosmate(VI); potassium carbonate; potassium hexacyanoferrate(III); In water; toluene; tert-butyl alcohol; at 0 ℃; for 16h; Title compound not separated from byproducts;

Reference yield:

methyl-2,3,4-tetra-O-benzyl-L-glycero-α-D-manno-heptopyranoside (122588-51-6) → ethyl 2,3,4-tri-O-benzyl-1-thio-L-glycero-α-D-manno-heptopyranoside (142270-27-7)

Guidance literature:

Multi-step reaction with 4 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

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

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

upstream raw materials:

ethyl 6,7-di-O-acetyl-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

methyl 6,7-di-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranoside

1,6,7-tri-O-acetyl-2,3,4-tri-O-benzyl-L-glycero-α-D-manno-heptopyranose

Downstream raw materials:

ethyl 6-O-benzoyl-2,3,4-tri-O-benzyl-7-O-(tert-butyldimethylsilyl)-1-thio-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