1-O-(phenylacetyl)-7-O-butyrylcastanospermine

Base Information

• Chemical Name: 1-O-(phenylacetyl)-7-O-butyrylcastanospermine
• CAS No.: 125880-34-4
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 125880-34-4.mol

Synonyms:1-O-(phenylacetyl)-7-O-butyrylcastanospermine

Chemical Property of 1-O-(phenylacetyl)-7-O-butyrylcastanospermine

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-O-(phenylacetyl)-7-O-butyrylcastanospermine

There total 3 articles about 1-O-(phenylacetyl)-7-O-butyrylcastanospermine 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: 58.0%

2,2,2-trichloroethyl butyrate (57392-44-6) + 1-O-(phenylacetyl)castanospermine (125880-25-3) → 1-O-(phenylacetyl)-6-O-butyrylcastanospermine (125880-33-3) + 1-O-(phenylacetyl)-7-O-butyrylcastanospermine (125880-34-4)

Guidance literature:

In tetrahydrofuran; at 45 ℃; for 72h; lipase from Chromobacterium viscosum;

DOI:10.1021/ja00164a001

Reference yield:

vinyl ester of phenylacetic acid (18120-64-4) → 1-O-(phenylacetyl)-7-O-butyrylcastanospermine (125880-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / subtilisin Carlsberg (EC 3.4.21.4) / pyridine / 96 h / 45 °C

2: 58 percent / tetrahydrofuran / 72 h / 45 °C / lipase from Chromobacterium viscosum

With subtilisin Carlsberg (EC 3.4.21.4); In tetrahydrofuran; pyridine;

DOI:10.1021/ja00164a001

Reference yield:

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine (79831-76-8) → 1-O-(phenylacetyl)-7-O-butyrylcastanospermine (125880-34-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 30 percent / subtilisin Carlsberg (EC 3.4.21.4) / pyridine / 96 h / 45 °C

2: 58 percent / tetrahydrofuran / 72 h / 45 °C / lipase from Chromobacterium viscosum

With subtilisin Carlsberg (EC 3.4.21.4); In tetrahydrofuran; pyridine;

DOI:10.1021/ja00164a001

upstream raw materials:

2,2,2-trichloroethyl butyrate

1-O-(phenylacetyl)castanospermine

vinyl ester of phenylacetic acid

(1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine

Refernces