(1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE

Base Information

• Chemical Name: (1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE
• CAS No.: 91897-68-6
• Molecular Formula: C₁₄H₁₉NO₇
• Molecular Weight: 313.307
• Mol file: 91897-68-6.mol

Synonyms:4,6,7-tri-O-acetyl-2,3,5,8-tetradeoxy-5,8-imino-D-manno-octono-1,5-lactam

Chemical Property of (1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE

Chemical Property:

• Boiling Point: 429.1±45.0 °C(Predicted)
• PKA: -5.41±0.70(Predicted)
• Density: 1.31±0.1 g/cm3(Predicted)
• Solubility.: Chloroform

Purity/Quality:

97% ^*data from raw suppliers

(1S,2R,8R,8aR)-1,2,8-Triacetoxy-octahydro-5-oxyindolizine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (1S,2R,8R,8aR)-1,2,8-Triacetoxy-octahydro-5-oxyindolizine (cas# 91897-68-6) is a compound useful in organic synthesis.

Technology Process of (1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE

There total 13 articles about (1S,2R,8R,8AR)-1,2,8-TRIACETOXY-OCTAHYDRO-5-OXYINDOLIZINE 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: 25.0%

ethyl 4,6,7-tri-O-acetyl-5,8-benzyloxycarbonylimino-2,3,5,8-tetradeoxy-D-manno-oct-2-enonate (91897-32-4) → 4,6,7-tri-O-acetyl-2,3,5,8-tetradeoxy-5,8-imino-D-manno-octono-1,5-lactam (91897-68-6) + ethyl 6,7-di-O-acetyl-5,8-acetylimino-2,3,5,8-tetradeoxy-D-manno-octonate (91897-34-6)

Guidance literature:

With hydrogen; palladium on activated charcoal; In ethanol; acetic acid; for 2h; under 3192 Torr;

Reference yield:

2,4,5-tri-O-acetyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-aldehydo-D-mannose (91897-31-3) → 4,6,7-tri-O-acetyl-2,3,5,8-tetradeoxy-5,8-imino-D-manno-octono-1,5-lactam (91897-68-6)

Guidance literature:

Multi-step reaction with 3 steps

2: H₂ / Pd/C

With hydrogen; palladium on activated charcoal;

DOI:10.1039/c39840000447

Reference yield:

(2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester (91897-30-2) → 4,6,7-tri-O-acetyl-2,3,5,8-tetradeoxy-5,8-imino-D-manno-octono-1,5-lactam (91897-68-6)

Guidance literature:

Multi-step reaction with 4 steps

1: HgCl₂, CdCO₃

3: H₂ / Pd/C

With cadmium(II) carbonate; hydrogen; mercury dichloride; palladium on activated charcoal;

DOI:10.1039/c39840000447

upstream raw materials:

ethyl 4,6,7-tri-O-acetyl-5,8-benzyloxycarbonylimino-2,3,5,8-tetradeoxy-D-manno-oct-2-enonate

(R)-4-Acetoxy-4-((2R,3S,4R)-3,4-diacetoxy-pyrrolidin-2-yl)-butyric acid ethyl ester

2,4,5-tri-O-acetyl-3,6-benzyloxycarbonylimino-3,6-dideoxy-aldehydo-D-mannose

(2S,3S,4R)-3,4-Diacetoxy-2-((S)-1-acetoxy-2,2-bis-ethylsulfanyl-ethyl)-pyrrolidine-1-carboxylic acid benzyl ester

Downstream raw materials:

swainsonine