(3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene

Base Information

• Chemical Name: (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene
• CAS No.: 214753-68-1
• Molecular Formula: C₂₃H₃₉NO₄Si
• Molecular Weight: 421.652
• Mol file: 214753-68-1.mol

Synonyms:(3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene

Chemical Property of (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene

There total 2 articles about (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene 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: 80.0%

tert-butyldimethylsilyl chloride (18162-48-6) + (3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene (214753-16-9) → (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene (214753-68-1)

Guidance literature:

With 1H-imidazole; In tetrahydrofuran; at 20 ℃; for 12h;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield:

N-carbobenzoxy-L-leucinal (70853-26-8,86852-22-4,71413-15-5) → (3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene (214753-68-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: t-BuLi / diethyl ether / 4 h / -78 - 0 °C

1.2: 54 percent / diethyl ether / 3.5 h / -78 - 0 °C

2.1: 80 percent / imidazole / tetrahydrofuran / 12 h / 20 °C

With 1H-imidazole; tert.-butyl lithium; In tetrahydrofuran; diethyl ether; 1.1: Metallation / 1.2: Addition / 2.1: Substitution;

DOI:10.1016/S0968-0896(98)00089-3

Reference yield: 93.0%

(3RS,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-hydroxy-6-methyl-1-heptene (214753-68-1) → (4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1-heptene (214753-22-7)

Guidance literature:

With oxalyl dichloride; dimethyl sulfoxide; triethylamine; In dichloromethane; at -78 - 20 ℃;

DOI:10.1016/S0968-0896(98)00089-3

upstream raw materials:

tert-butyldimethylsilyl chloride

(3RS,4S)-4-benzyloxycarbonylamino-3-hydroxy-2-hydroxymethyl-6-methyl-1-heptene

N-carbobenzoxy-L-leucinal

Downstream raw materials:

(4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1-heptene

(2R,4S)-4-benzyloxycarbonylamino-2-tert-butyldimethylsiloxymethyl-3-oxo-6-methyl-1,2-oxiranylheptane

(2R,4S)-2-tert-butyldimethylsiloxymethyl-4-[(S)-O-tertbutyldiphenylsiloxymethyl-N-(6-N-fluorenylmethoxycarbonyl)serylamino]-6-methyl-1,2-oxiranylheptane