(3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Base Information

• Chemical Name: (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester
• CAS No.: 129919-83-1
• Molecular Formula: C₄₁H₇₇NO₈Si₂
• Molecular Weight: 768.235

Synonyms:(3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Chemical Property of (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

There total 18 articles about (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl 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: 93.0%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-hydroxy-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (126587-70-0) → (3R,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (130008-94-5) + (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (129919-83-1)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3h;

DOI:10.1021/ja00177a030

Reference yield:

(3S,4S,5R)-6-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol acetate (126587-53-9) → (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (129919-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pentafluorophenyl trifluoroacetate, pyridine, 2.) LDA / 1.) CH₂Cl₂, 2.) THF

2: 83 percent / KBH₄ / ethanol

3: 2,6-lutidine

With pyridine; 2,6-dimethylpyridine; potassium borohydride; pentafluorophenyl trifloroacetate; lithium diisopropyl amide; In ethanol;

DOI:10.1021/jo00097a022

Reference yield:

N-benzyloxycarbonylamino-D-alloisoleucine (3160-59-6,4276-05-5,28862-89-7,55723-45-0,55723-48-3,127866-12-0) → (3S,4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-<(triisopropylsilyl)oxy>-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester (129919-83-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) pentafluorophenyl trifluoroacetate, pyridine, 2.) LDA / 1.) CH₂Cl₂, 2.) THF

2: 83 percent / KBH₄ / ethanol

3: 2,6-lutidine

With pyridine; 2,6-dimethylpyridine; potassium borohydride; pentafluorophenyl trifloroacetate; lithium diisopropyl amide; In ethanol;

DOI:10.1021/jo00097a022

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(4R,5S)-4-<<(benzyloxy)carbonyl>amino>-3-hydroxy-5-methyl-heptanoic acid, (1S,2S,3R)-4-<(tert-butyldimethylsilyl)oxy>-1-isopropyl-2-(methoxymethoxy)-3-methylbutyl ester

N-benzyloxycarbonylamino-D-alloisoleucine

(3S,4S,5R)-6-[(tert-butyldimethylsilyl)oxy]-4-(methoxymethoxy)-2,5-dimethyl-3-hexanol acetate

Downstream raw materials:

N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-

N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3S)-1-isopropyl-2-

C₆₆H₁₀₇N₅O₁₆Si

N-<1--L-leucyl>-L-prolyl>-3-(p-methoxyphenyl)-N-methyl-L-alanine, ester with (3S,4R,5S)-3-<(triisopropylsilyl)oxy>-4-<(2S,3R)-2-<(tert-butoxycarbonyl)amino>-3-hydroxybutyramido>-5-methylheptanoic acid, (1S,2S,3R)-4-hydroxy-1-isop

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