(2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol

Base Information

• Chemical Name: (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol
• CAS No.: 937166-60-4
• Molecular Formula: C₂₄H₃₆O₆Si
• Molecular Weight: 448.632
• Mol file: 937166-60-4.mol

Synonyms:(2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol

Chemical Property of (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol

There total 4 articles about (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol 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: 100.0%

tert-butylchlorodiphenylsilane (58479-61-1) + (2R,3R)-2,3-bis(methoxymethoxy)butane-1,4-diol (166734-76-5) → (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol (937166-60-4)

Guidance literature:

(2R,3R)-2,3-bis(methoxymethoxy)butane-1,4-diol; With n-butyllithium; In tetrahydrofuran;

tert-butylchlorodiphenylsilane; In tetrahydrofuran;

DOI:10.1021/ja050728l

Reference yield: 99.0%

(-)-(2S,3S)-2,3-bis(methoxymethoxy)butane-1,4-diol (99891-36-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol (937166-60-4)

Guidance literature:

(-)-(2S,3S)-2,3-bis(methoxymethoxy)butane-1,4-diol; With n-butyllithium; In tetrahydrofuran; at 0 ℃; for 0.5h; Inert atmosphere;

tert-butylchlorodiphenylsilane; In tetrahydrofuran; at 0 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.08.126

Reference yield:

diethyl (2S,3S)-2,3-di-O-methoxymethyl-tartrate (159593-22-3) → (2S,3S)-4-(tert-butyl(diphenyl)silyloxy)-2,3-bis(methoxymethoxy)butan-1-ol (937166-60-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 86 percent / LAH / diethyl ether

2.1: n-BuLi / tetrahydrofuran

2.2: 100 percent / tetrahydrofuran

With lithium aluminium tetrahydride; n-butyllithium; In tetrahydrofuran; diethyl ether;

DOI:10.1021/ja050728l

upstream raw materials:

tert-butylchlorodiphenylsilane

(2R,3R)-2,3-bis(methoxymethoxy)butane-1,4-diol

(-)-(2S,3S)-2,3-bis(methoxymethoxy)butane-1,4-diol

(+)-(2R,3R)-diethyl 2,3-bismethoxymethoxybutanedioate

Downstream raw materials:

(2R,3S)-4-(tert-Butyl-diphenyl-silanyloxy)-2,3-bis-methoxymethoxy-butyraldehyde

(4S,5S,6R)-5,6-dihydroxy-3,3-dimethyl-7-[(1,1-dimethylethyl)diphenylsilyl]oxy-4-methoxy-1-heptene

(2R,3S,4S)-1-(tert-Butyl-diphenyl-silanyloxy)-4-methoxy-3-methoxymethoxy-5,5-dimethyl-hept-6-en-2-ol

(((2R,3R,4S,6R)-6-allyl-tetrahydro-4-methoxy-3-(methoxymethoxy)-5,5-dimethyl-2H-pyran-2-yl)methoxy)(tert-butyl)diphenylsilane