(2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol

Base Information

• Chemical Name: (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol
• CAS No.: 827603-04-3
• Molecular Formula: C₂₂H₄₀O₅Si
• Molecular Weight: 412.642
• Mol file: 827603-04-3.mol

Synonyms:(2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol

Chemical Property of (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol

There total 4 articles about (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol 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: 99.0%

(2S,4S,5R)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethylhexan-3-one (827603-03-2) → (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol (827603-04-3)

Guidance literature:

With camphor-10-sulfonic acid; acetic acid; tetramethylammonium triacetoxyborohydride; In acetonitrile; at -40 - -22 ℃; for 18h;

DOI:10.1021/jo048534w

Reference yield:

1-(tert-butyl-dimethyl-silanyloxy)propane-1,2-diol (85951-08-2) → (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol (827603-04-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium periodate / CH₂Cl₂; H₂O / 3 h / 20 °C

2.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2 h / 0 °C

2.2: 94 percent / diethyl ether / 1.25 h / -78 - 0 °C

3.1: 99 percent / Me₄NHB(OAc)3; acetic acid; camphorsulfonic acid / acetonitrile / 18 h / -40 - -22 °C

With sodium periodate; camphor-10-sulfonic acid; dicyclohexylboron chloride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; dichloromethane; water; acetonitrile;

DOI:10.1021/jo048534w

Reference yield:

tert-butyldimethylsiloxyacetaldehyde (102191-92-4) → (2R,3R,4S,5S)-1-(tert-butyldimethylsilyloxy)-6-(4-methoxybenzyloxy)-3,5-dimethyl-hexane-2,4-diol (827603-04-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dicyclohexylboron chloride; triethylamine / diethyl ether / 2 h / 0 °C

1.2: 94 percent / diethyl ether / 1.25 h / -78 - 0 °C

2.1: 99 percent / Me₄NHB(OAc)3; acetic acid; camphorsulfonic acid / acetonitrile / 18 h / -40 - -22 °C

With camphor-10-sulfonic acid; dicyclohexylboron chloride; acetic acid; triethylamine; tetramethylammonium triacetoxyborohydride; In diethyl ether; acetonitrile;

DOI:10.1021/jo048534w

upstream raw materials:

(2S,4S,5R)-6-(tert-butyldimethylsilyloxy)-5-hydroxy-1-(4-methoxybenzyloxy)-2,4-dimethylhexan-3-one

1-(tert-butyl-dimethyl-silanyloxy)propane-1,2-diol

tert-butyldimethylsiloxyacetaldehyde

tert-butyldimethylsilyl chloride

Downstream raw materials:

(2S,3R,4S)-5-[(4-methoxybenzyl)oxy]-2,4-dimethylpentane-1,3-diol

methyl (2R,3S,4S)-2,4-dimethyl-3-hydroxy-5-(4-methoxybenzyloxy)pentanoate

(+)-(Z)-(2S,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dien-1-ol

(+)-(Z)-(2R,3S,4S)-3-(4-methoxybenzyloxy)-2,4-dimethylocta-5,7-dienal