(2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one

Base Information

• Chemical Name: (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one
• CAS No.: 1360866-46-1
• Molecular Formula: C₄₁H₆₂O₉Si₂
• Molecular Weight: 755.109

Synonyms:(2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one

Chemical Property of (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one

There total 10 articles about (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one 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%

(4S,5R,E)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-hex-2-en-1-one (1360866-45-0) → (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one (1360866-46-1)

Guidance literature:

With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In water; acetone; tert-butyl alcohol; at 0 ℃; for 30h; Inert atmosphere;

DOI:10.1021/jo202353r

Reference yield:

1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)ethanone (1360866-36-9) → (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one (1360866-46-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

1.3: 1 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / Inert atmosphere; Reflux; Cooling with ice

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 30 h / 0 °C / Inert atmosphere

With osmium(VIII) oxide; titanium tetrachloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo202353r

Reference yield:

(2R,3R)-2,4-bis-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-butanal (1360866-43-8) → (2S,3S,4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-2,3-dihydroxyhexan-1-one (1360866-46-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: titanium tetrachloride / dichloromethane / 0.08 h / -78 °C / Inert atmosphere

1.2: 0.25 h / -78 °C / Inert atmosphere

1.3: 1 h / 20 °C / Inert atmosphere

2.1: triethylamine / dichloromethane / 1 h / Inert atmosphere; Reflux; Cooling with ice

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0.5 h / 0 °C / Inert atmosphere

4.1: osmium(VIII) oxide; 4-methylmorpholine N-oxide / water; acetone; tert-butyl alcohol / 30 h / 0 °C / Inert atmosphere

With osmium(VIII) oxide; titanium tetrachloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/jo202353r

upstream raw materials:

(2R,3R)-2,4-bis-(benzyloxy)-3-(tert-butyldimethylsilyloxy)-butanal

(4S,5R)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-3-hydroxyhexan-1-one

(4S,5R,E)-4,6-bis-(benzyloxy)-5-(tert-butyldimethylsilyloxy)-1-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-hex-2-en-1-one

1-(2-(hydroxymethyl)-4,6-dimethoxyphenyl)ethanol

Downstream raw materials:

((4R,5S)-5-((1S,2R)-1,3-bis-(benzyloxy)-2-(tert-butyldimethylsilyloxy)propyl)-2,2-dimethyl-1,3-dioxolan-4-yl)-(2-((tert-butyldimethylsilyloxy)methyl)-4,6-dimethoxyphenyl)-methanone

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