[1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate)

Base Information

• Chemical Name: [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate)
• CAS No.: 134100-32-6
• Molecular Formula: C₂₇H₂₈BrNO₉
• Molecular Weight: 590.425

Synonyms:[1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate)

Chemical Property of [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate)

Chemical Property:

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Technology Process of [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate)

There total 5 articles about [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate) 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: 85.0%

[1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 6-benzylcarbonate 7-(4-bromobenzoate) (139416-61-8) → [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate) (134100-32-6)

Guidance literature:

With acetic anhydride; In pyridine; ethyl acetate;

Reference yield:

1,8-O-isopropylidenylcastanospermine (130446-91-2) → [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate) (134100-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Et₃N / tetrahydrofuran

2: 84 percent / Et₃N

3: 1) HCl, 2) pyridine / 1) MeOH

With pyridine; hydrogenchloride; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74866-0

Reference yield:

benzyl chloroformate (501-53-1,94274-21-2) → [1S-(1α,6β,7α,8β,8aβ)]-octahydro-1,6,7,8-indolizinetetrol 1,8-diacetate 6-benzylcarbonate 7-(4-bromobenzoate) (134100-32-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Et₃N / tetrahydrofuran

2: 84 percent / Et₃N

3: 1) HCl, 2) pyridine / 1) MeOH

With pyridine; hydrogenchloride; triethylamine; In tetrahydrofuran;

DOI:10.1016/S0040-4039(00)74866-0

upstream raw materials:

acetic anhydride

4-Bromo-benzoic acid (3aS,8S,9R,9aR,9bR)-8-benzyloxycarbonyloxy-2,2-dimethyl-octahydro-[1,3]dioxino[4,5,6-hi]indolizin-9-yl ester

1,8-O-isopropylidenylcastanospermine

6-O-carbobenzyloxy-1,8-O-isopropylidenecastanospermine

Downstream raw materials:

6-acetamido-6-deoxycastanospermine

6-amino-6-deoxycastanospermine

1,8-di-O-acetyl-7-O-benzoylcastanospermine

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