(1R,2R,3S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol

Base Information

• Chemical Name: (1R,2R,3S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol
• CAS No.: 119065-82-6
• Molecular Formula: C₈H₁₅NO₄
• Molecular Weight: 189.211
• Mol file: 119065-82-6.mol

Synonyms:1H-Pyrrolizine-1,2,7-triol,hexahydro-3-(hydroxymethyl)-, [1R-(1a,2b,3b,7b,7aa)]-; (+)-3-Epiaustraline; 3,7a-Diepialexine; 3,8-Di-epi-alexine;3,8-Diepialexine; 3-Epiaustraline; 3-epi-Australine

Chemical Property of (1R,2R,3S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol

Chemical Property:

• Vapor Pressure: 1.03E-08mmHg at 25°C
• Boiling Point: 417.4°C at 760 mmHg
• Flash Point: 263.5°C
• Density: 1.53g/cm³

Purity/Quality:

≥98% by HPLC ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (1R,2R,3S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol

There total 5 articles about (1R,2R,3S,7S,7aR)-3-(hydroxymethyl)hexahydro-1H-pyrrolizine-1,2,7-triol 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: 96.0%

6,6-di-tert-butyl-2-(tert-butyl-dimethyl-silanyloxymethyl)-hexahydro-5,7-dioxa-2a-aza-6-sila-cyclopenta[cd]inden-1-ol → 3-epi-australine (119065-82-6)

Guidance literature:

With hydrogen fluoride; In methanol; for 24h;

DOI:10.1021/ja9829970

Reference yield: 88.0%

(1S,5S,6R,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)hexahydro-1H-pyrrolizin-1-ol (1204748-41-3) → 3-epi-australine (119065-82-6)

Guidance literature:

(1S,5S,6R,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)hexahydro-1H-pyrrolizin-1-ol; With hydrogen; palladium dichloride; In methanol; at 20 ℃; for 3h;

With hydrogenchloride; In methanol; water; at 20 ℃; for 21h;

DOI:10.1021/jo902355p

Reference yield: 70.0%

N-((2S,3S,4R,5S)-2-Allyl-4,5,6-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-formamide (314057-09-5) → 3-epi-australine (119065-82-6)

Guidance literature:

N-((2S,3S,4R,5S)-2-Allyl-4,5,6-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-formamide; With ozone; In methanol; at -78 ℃;

With hydrogen; 10percent Pd/C; In methanol; at -78 ℃;

With hydrogenchloride; hydrogen; 10percent Pd/C; In 1,4-dioxane; methanol; water; for 72h; Further stages.;

DOI:10.1021/jo000933d

upstream raw materials:

3-epiaustralien tetraacetate

N-((2S,3S,4R,5S)-2-Allyl-4,5,6-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-3-yl)-formamide

(1S,5S,6R,7R,7aR)-6,7-bis(benzyloxy)-5-((tert-butyldimethylsilyloxy)methyl)hexahydro-1H-pyrrolizin-1-ol