2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose

Base Information

• Chemical Name: 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose
• CAS No.: 77451-22-0
• Molecular Formula: C₂₈H₂₃NO₇
• Molecular Weight: 485.493
• Mol file: 77451-22-0.mol

Synonyms:2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose

Chemical Property of 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose

There total 3 articles about 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose 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: 30.0%

mercury(II) cyanide (592-04-1) + 2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide (14218-08-7,41881-44-1,53297-33-9,60820-93-1,61198-82-1,67986-91-8,73068-86-7,131897-72-8,131897-73-9) → 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-β-L-manno-hexopyranose (77451-23-1) + 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose (77451-22-0)

Guidance literature:

In nitromethane; for 72h;

DOI:10.1021/jm00143a006

Reference yield:

1,2,3,4-tetra-O-benzoyl-α/β-L-rhamnopyranose (61198-83-2,73891-00-6,73891-01-7,113567-33-2,113567-34-3,122089-70-7,135266-93-2,135266-94-3,140223-15-0,141115-69-7,148152-57-2,71155-57-2) → 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose (77451-22-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 77 percent / hydrobromic acid / acetic acid / 4 °C

2: 62 percent / nitromethane / 72 h

With hydrogen bromide; In nitromethane; acetic acid;

DOI:10.1021/jm00143a006

Reference yield:

mercury(II) cyanide (592-04-1) + p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside (73068-86-7) → 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-β-L-manno-hexopyranose (77451-23-1) + 2,3,4-tri-O-benzoyl-1-cyano-6-deoxy-α-L-manno-hexopyranose (77451-22-0)

Guidance literature:

In nitromethane; at 20 ℃; for 70h; Yield given;

DOI:10.1016/S0040-4039(00)74533-3

upstream raw materials:

mercury(II) cyanide

p-tolyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl bromide

1,2,3,4-tetra-O-benzoyl-α/β-L-rhamnopyranose

Downstream raw materials:

Benzoic acid (2S,3S,4S)-6-cyano-3-hydroxy-2-methyl-3,4-dihydro-2H-pyran-4-yl ester

2-(2',3',4'-tri-O-benzoyl-6'-deoxy-α-L-manno-hexopyranosyl)-6-nitro<1,2,4>triazolo<1,5-a>pyridine

2-(2',3',4'-tri-O-benzoyl-6'-deoxy-α-L-manno-hexopyranosyl)-6-amino<1,2,4>triazolo<1,5-a>pyridine

2-(2',3',4'-tri-O-benzoyl-6'-deoxy-α-L-manno-hexopyranosyl)-8-amino<1,2,4>triazolo<1,5-a>pyridine

Refernces

• 1、 Huynh-Dinh, T.,Gouyette, C.,Igolen, J.. "CYANO-1 CETO-3 ET -4 L-RHAMNOSES". . p. 4499 - 4502. Retrieved 2007/10/02.