(4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol

Base Information

• Chemical Name: (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol
• CAS No.: 1333236-95-5
• Molecular Formula: C₁₉H₃₄O₃Si
• Molecular Weight: 338.563
• Mol file: 1333236-95-5.mol

Synonyms:(4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol

Chemical Property of (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol

There total 8 articles about (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-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: 95.0%

{[(2S,3R)-3-(benzyloxy)hex-5-en-2-yl]oxy}(tert-butyl)dimethylsilane → (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol (1333236-95-5)

Guidance literature:

{[(2S,3R)-3-(benzyloxy)hex-5-en-2-yl]oxy}(tert-butyl)dimethylsilane; With dimethylsulfide borane complex; In tetrahydrofuran; at 20 ℃; for 4h; Inert atmosphere;

With dihydrogen peroxide; sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 13h;

DOI:10.1002/ejoc.201300302

Reference yield: 90.0%

(5S,6R)-6-(benzyloxy)-2,2,3,3,5,11,11,12,12-nonamethyl-4,10-dioxa-3,11-disilatridecane (1333236-88-6) → (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol (1333236-95-5)

Guidance literature:

With pyridine; pyridine hydrofluoride; In tetrahydrofuran; at 0 ℃; for 1.25h; Inert atmosphere;

DOI:10.1002/anie.201102521

Reference yield:

(2S,3R)-2-(tert-butyldimethylsilyloxy)hex-5-en-3-ol (471914-70-2) → (4R,5S)-4-(benzyloxy)-5-[(tert-butyldimethylsilyl)oxy]hexan-1-ol (1333236-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.25 h / 0 °C / Inert atmosphere

1.2: 2 h / 20 °C / Inert atmosphere

2.1: dimethylsulfide borane complex / tetrahydrofuran / 4 h / 20 °C / Inert atmosphere

2.2: 13 h / 20 °C

With dimethylsulfide borane complex; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1002/ejoc.201300302

upstream raw materials:

(5S,6R)-2,2,3,3,5,11,11,12,12-nonamethyl-4,10-dioxa-3,11-disilatridecan-6-ol

(5S,6R)-6-(benzyloxy)-2,2,3,3,5,11,11,12,12-nonamethyl-4,10-dioxa-3,11-disilatridecane

ethyl (S)-2-(tert-butyldimethylsilyloxy)propanoate

(S)-2-tert-butyl-dimethyl-silanyloxy propanal

Downstream raw materials:

((2S,3R)-3-(benzyloxy)-6-iodohexan-2-yloxy)(tert-butyl)dimethylsilane

((4R,5S)-4-(benzyloxy)-5-(tert-butyldimethylsilyloxy)hexyl)triphenylphosphonium iodide

C₃₅H₅₉ClO₆Si₂

((2S,3S)-3-((1R,2S,4S,9R,10S,z)-9-(benzyloxy)-4,10-bis(tert-butyldimethylsilyloxy)-1,2-dichloroundec-5-enyl)oxiran-2-yl)methyl acetate