(Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside

Base Information

• Chemical Name: (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside
• CAS No.: 137793-90-9
• Molecular Formula: C₃₀H₃₂O₇
• Molecular Weight: 504.58
• Mol file: 137793-90-9.mol

Synonyms:(Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside

Chemical Property of (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside

There total 8 articles about (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside 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%

acetic anhydride (108-24-7) + methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-90-9)

Guidance literature:

With potassium carbonate; In acetonitrile;

DOI:10.1039/a800282g

Reference yield: 85.0%

acetic anhydride (108-24-7) + methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → (E)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-91-0) + (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-90-9)

Guidance literature:

With potassium carbonate; In acetonitrile; at 80 ℃; Yields of byproduct given;

DOI:10.1021/ja00026a042

Reference yield:

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside (53008-65-4,641635-63-4) → (Z)-methyl 6-O-acetyl-2,3,4-tri-O-benzyl-α-D-gluco-hex-5-enopyranoside (137793-90-9)

Guidance literature:

Multi-step reaction with 2 steps

1: N,N-dicyclohexylcarbodiimide; trifluoroacetic acid; pyridine / dimethylsulfoxide; benzene / 24 h / 20 °C

2: Et₃N; 4-(dimethylamino)pyridine / 1,2-dichloro-ethane / 3 h / Heating

With pyridine; dmap; triethylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; In dimethyl sulfoxide; 1,2-dichloro-ethane; benzene;

DOI:10.1021/jo001575h

upstream raw materials:

acetic anhydride

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-D-glucopyranoside

methyl 2,3,4-tri-O-benzyl-6-O-trityl-α-D-glucopyranoside

Downstream raw materials:

(1R,2S,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate

(1R,2R,3S,4R,5S)-3,4,5-tribenzyloxy-2-hydroxy-6-oxocyclohexyl acetate

C₃₅H₄₂O₁₁

C₆₃H₅₈O₁₅