phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside

Base Information

• Chemical Name: phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside
• CAS No.: 138857-83-7
• Molecular Formula: C₃₀H₂₈O₉S
• Molecular Weight: 564.613
• Mol file: 138857-83-7.mol

Synonyms:phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside

Chemical Property of phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside

There total 14 articles about phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside 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%

pyruvic acid methyl ester (600-22-6) + phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside (138857-53-1) → phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside (138857-83-7)

Guidance literature:

With boron trifluoride diethyl etherate; In acetonitrile; for 2.5h; Ambient temperature;

DOI:10.1016/0008-6215(94)80063-4

Reference yield: 37.0%

pyruvic acid methyl ester (600-22-6) + phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside (138857-53-1) → phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside (138857-83-7) + (2S,4aR,6S,7R,8S,8aS)-7,8-Bis-benzoyloxy-2-methyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine-2-carboxylic acid methyl ester (138857-84-8)

Guidance literature:

With boron trifluoride diethyl etherate; Title compound not separated from byproducts; Ambient temperature;

DOI:10.1016/0040-4039(94)85023-2

Reference yield:

1-thiophenyl-β-D-galactopyranoside (16758-34-2) → phenyl 4,6-O-[1-(R)-(methoxycarbonyl)ethylidene]-2,3-di-O-benzoyl-1-thio-β-D-galactopyranoside (138857-83-7)

Guidance literature:

Multi-step reaction with 4 steps

1: camphorsulfonic acid / dimethylformamide / 2 h / 50 °C

2: 90 percent / pyridine

3: 80 percent / aq. HOAc

4: 64 percent / BF₃*OEt₂ / acetonitrile / Ambient temperature

With pyridine; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; acetic acid; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1080/07328309808002904

upstream raw materials:

pyruvic acid methyl ester

phenyl 2,3-di-O-benzoyl-1-thio-β-D-galactoypyranoside

1-thiophenyl-β-D-galactopyranoside

1-deoxy-1-(phenylthio)-2,3,4,6-tetra-O-acetyl-β-D-galactopyranose

Downstream raw materials:

5-<(benzyloxycarbonyl)amino>pentyl 2,3-di-O-benzoyl-4,6-O<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranoside

2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl bromide

2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-β-D-galactopyranosyl fluoride

2,3-di-O-benzoyl-4,6-O-<(R)-1-methoxycarbonylethylidene>-α-D-galactopyranosyl fluoride