(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

Base Information

• Chemical Name: (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester
• CAS No.: 139190-55-9
• Molecular Formula: C₃₁H₄₀O₅Si
• Molecular Weight: 520.741
• Mol file: 139190-55-9.mol

Synonyms:(3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

Chemical Property of (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester

There total 3 articles about (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl 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: 94.0%

methyllithium (917-54-4) + Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5) → (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester (139190-55-9)

Guidance literature:

With copper(l) iodide; chloro-trimethyl-silane; In tetrahydrofuran;

DOI:10.1016/S0040-4039(99)00783-2

Reference yield: 92.0%

methyllithium-lithium bromide + Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5) → (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester (139190-55-9)

Guidance literature:

methyllithium-lithium bromide; With copper(l) iodide; In tetrahydrofuran; diethyl ether; at -15 - 0 ℃; for 0.5h;

Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate; With chloro-trimethyl-silane; In tetrahydrofuran; diethyl ether; at -78 ℃; for 3h;

DOI:10.1021/ja970251g

Reference yield:

methyllithium-lithium bromide + Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate (139190-51-5) → Methyl (3R,4S)-4-(benzyloxymethoxy)-5-tert-butyldiphenylsiloxy-3-methylpentanoate (139190-56-0) + (3S,4S)-4-[(benzyloxy)methoxy]-5-(tert-butyldiphenylsilanyloxy)-3-methylpentanoic acid methyl ester (139190-55-9)

Guidance literature:

With copper(l) iodide; chloro-trimethyl-silane; multistep reaction: diastereoselectivity in the conjugate addition of Me2CuLi; other γ-alkoxy- and γ-ureido α,β-unsaturated esters and Li alkyl cuprates;

DOI:10.1055/s-1991-28396

upstream raw materials:

Methyl (4S,E)-4-(benzyloxymethoxy)-5-(tert-butyldiphenylsiloxy)-2-pentenoate

methyllithium

Downstream raw materials:

(3S,4S)-4-Benzyloxymethoxy-5-(tert-butyl-diphenyl-silanyloxy)-3-methyl-pentan-1-ol