tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate

Base Information

• Chemical Name: tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate
• CAS No.: 1175565-50-0
• Molecular Formula: C₃₀H₅₃NO₅Si
• Molecular Weight: 535.84

Synonyms:tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate

Chemical Property of tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate

Chemical Property:

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Technology Process of tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate

There total 1 articles about tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate 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: 68.0%

(5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone (1175565-49-7) + 6-(tert-butyldimethylsilanyloxy)-1-hexylmagnesium bromide (267898-36-2) → tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate (1175565-50-0)

Guidance literature:

In tetrahydrofuran; dichloromethane; at -78 - -50 ℃; for 2.66667h; regioselective reaction;

DOI:10.1016/j.tetasy.2009.04.008

Reference yield: 90.0%

tert-butyl [(2S,3S)-3-benzyloxy-12-(tert-butyldimethylsilyloxy)-6-oxododecan-2-yl]carbamate (1175565-50-0) → tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate (1175565-51-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1016/j.tetasy.2009.04.008

upstream raw materials:

(5S,6S)-5-benzyloxy-1-(tert-butyloxycarbonyl)-6-methyl-2-piperidinone

6-(tert-butyldimethylsilanyloxy)-1-hexylmagnesium bromide

Downstream raw materials:

tert-butyl [(2S,3S)-3-benzyloxy-12-hydroxy-6-oxododecan-2-yl]carbamate

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