(1R,6S,7S,8S,8aS)-octahydroindolizine-1,6,7,8-tetrol

Base Information

• Chemical Name: (1R,6S,7S,8S,8aS)-octahydroindolizine-1,6,7,8-tetrol
• CAS No.: 117894-11-8
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.211
• Mol file: 117894-11-8.mol

Synonyms:1,6,7,8-Indolizinetetrol,octahydro-, [1R-(1a,6a,7a,8b,8ab)]-; L-6-Epicastanospermine

Chemical Property of (1R,6S,7S,8S,8aS)-octahydroindolizine-1,6,7,8-tetrol

Chemical Property:

• Vapor Pressure: 6.94E-09mmHg at 25°C
• Boiling Point: 421.9°Cat760mmHg
• Flash Point: 267.6°C
• Density: 1.53g/cm³

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,6S,7S,8S,8aS)-octahydroindolizine-1,6,7,8-tetrol

There total 16 articles about (1R,6S,7S,8S,8aS)-octahydroindolizine-1,6,7,8-tetrol 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: 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: 84.0%

(3aS,8R,8aR,9S,9aS)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizine (121194-98-7) → L-6-epicastanospermine (117894-11-8)

Guidance literature:

With trifluoroacetic acid;

DOI:10.1016/0040-4039(88)85305-X

Reference yield:

(1aR,5R,5aS,6S,6aR)-6-Benzyloxy-5-hydroxy-hexahydro-1-oxa-2a-aza-cyclopropa[f]inden-2-one (123190-75-0,131722-87-7) → (+/-)-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:

Multi-step reaction with 4 steps

1: acetonitrile; H₂O / 4.5 h / 100 °C

2: 4-dimethylaminopyridine / pyridine / 48 h / 20 °C

3: 95 percent / BH₃*Me₂S / CH₂Cl₂ / 15 h / 20 °C

4: 97 percent / H₂ / 10percent Pd-C / tetrahydrofuran; H₂O / 24 h / 20 °C

With dmap; dimethylsulfide borane complex; hydrogen; palladium on activated charcoal; In tetrahydrofuran; pyridine; dichloromethane; water; acetonitrile;

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

upstream raw materials:

(3aS,8R,8aR,9S,9aR)-8-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizin-9-ol

6-O-tert-butyldimethylsilyl-2,3-O-isopropylidene-L-mannono-δ-lactam

N-benzyl-4-O-benzyl-6-O-tert-butyldimethylsilyl-1,5,7-trideoxy-1,5-imino-2,3-O-isopropylidene-L-glycero-L-manno-octitol

(3aS,8R,8aR,9S,9aS)-9-Benzyloxy-8-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-octahydro-[1,3]dioxolo[4,5-f]indolizine