benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester

Base Information

• Chemical Name: benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester
• CAS No.: 412960-87-3
• Molecular Formula: C₂₅H₄₃NO₅Si
• Molecular Weight: 465.706

Synonyms:benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester

Chemical Property of benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester

Chemical Property:

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Technology Process of benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester

There total 4 articles about benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester 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: 78.0%

isopropylmagnesium chloride (1068-55-9) + 2-[1-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester (412960-86-2) → benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester (412960-87-3)

Guidance literature:

With copper(I) bromide dimethylsulfide complex;

DOI:10.1016/S0040-4039(01)02206-7

Reference yield:

(2S,3R)-O(1)-benzyl-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-94-2) → benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester (412960-87-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 87 percent / H₂ / Pd/C

2: 92 percent / pyridine

3: 85 percent / NaH

4: 78 percent / CuBr*SMe₂

With pyridine; copper(I) bromide dimethylsulfide complex; hydrogen; sodium hydride; palladium on activated charcoal;

DOI:10.1016/S0040-4039(01)02206-7

Reference yield:

(2S,3R)-N(2)-(tert-butoxycarbonyl)-O(3)-benzoyl-O(4)-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol (371257-96-4) → benzoic acid 2-tert-butoxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxymethyl)-4-methyl-pentyl ester (412960-87-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 92 percent / pyridine

2: 85 percent / NaH

3: 78 percent / CuBr*SMe₂

With pyridine; copper(I) bromide dimethylsulfide complex; sodium hydride;

DOI:10.1016/S0040-4039(01)02206-7

upstream raw materials:

isopropylmagnesium chloride

2-[1-benzoyloxy-2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-aziridine-1-carboxylic acid tert-butyl ester

(2S,3R)-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

(2S,3R)-O⁽¹⁾-benzyl-N⁽²⁾-(tert-butoxycarbonyl)-O⁽³⁾-benzoyl-O⁽⁴⁾-(tert-butyldimethylsilyl)-2-amino-1,3,4-butanetriol

Downstream raw materials:

Benzoic acid (1R,2S)-2-tert-butoxycarbonylamino-4-methyl-1-(toluene-4-sulfonyloxymethyl)-pentyl ester

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