1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)-

Base Information

• Chemical Name: 1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)-
• CAS No.: 89955-60-2
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.211
• Mol file: 89955-60-2.mol

Synonyms:1,6,7,8-Indolizinetetrol,octahydro-, [1R-(1a,6a,7b,8a,8aa)]-; (+)-1-epi-Castanospermine; 1-Epicastanospermine;1-epi-Castanospermine

Chemical Property of 1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)-

There total 111 articles about 1,6,7,8-Indolizinetetrol, octahydro-, (1R,6S,7R,8R,8aR)- 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: 100.0%

(1R,6S,7R,8R,8aR)-1,6,7,8-tetrakis(benzyloxy)octahydroindolizidine (1004999-45-4) → 1-epi-castanospermine (89955-60-2)

Guidance literature:

With formic acid; palladium on activated charcoal; In methanol;

DOI:10.1016/j.tetlet.2007.11.033

Reference yield: 97.0%

(1R,6R,7S,8S,8aS)-8-Benzyloxy-octahydro-indolizine-1,6,7-triol (123190-77-2,131722-89-9) → (+/-)-castanospermin (79831-76-8,89955-60-2,107244-34-8,111467-11-9,117894-10-7,117894-11-8,121250-62-2,123284-48-0,129445-66-5,130983-46-9,139014-22-5,139014-23-6,139014-24-7,140386-64-7,140386-65-8,142393-60-0,142394-39-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In tetrahydrofuran; water; at 20 ℃; for 24h;

DOI:10.1016/S0040-4039(01)80287-2

Reference yield: 97.0%

6,7,8-tri-O-benzyl-1-epi-castanospermine → 1-epi-castanospermine (89955-60-2)

Guidance literature:

With hydrogenchloride; palladium 10% on activated carbon; hydrogen; In methanol; for 24h;

DOI:10.1016/j.cclet.2017.05.013

upstream raw materials:

(1R,6S,7R,8R,8aR)-1,6,7,8-tetrahydroxyhexahydroindolizin-3-one

(3aS,8R,8aS,9R,9aS)-8-(tert-Butyl-dimethyl-silanyloxy)-9-hydroxy-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5-f]indolizin-6-one

<1R,6S,7S,8R,8aR>-1-Hydroxy-6,7-(isopropylidenedioxy)-8-(methoxymethoxy)indolizidine

(2R,3R)-3-Hydroxy-2-((3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-pyrrolidine-1-carboxylic acid benzyl ester