(2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol

Base Information

• Chemical Name: (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol
• CAS No.: 883972-87-0
• Molecular Formula: C₂₆H₃₈O₄Si
• Molecular Weight: 442.671
• Mol file: 883972-87-0.mol

Synonyms:(2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol

Chemical Property of (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol

There total 5 articles about (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-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: 81.0%

tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane (883972-86-9) → (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol (883972-87-0)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; for 1h;

DOI:10.1002/ejoc.200500614

Reference yield:

(2R,3S,4R)-2,3-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-hex-5-enal → (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol (883972-87-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 544 mg / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

2: 69 percent / imidazole / dimethylformamide

3: 81 percent / DDQ; water / CH₂Cl₂ / 1 h

With 1H-imidazole; lithium aluminium tetrahydride; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500614

Reference yield:

(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)-hex-5-en-1-ol (883972-84-7) → (2R,3S,4R)-2,3-bis(benzyloxy)-1-(tert-butyldimethylsilyloxy)hex-5-en-4-ol (883972-87-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 69 percent / imidazole / dimethylformamide

2: 81 percent / DDQ; water / CH₂Cl₂ / 1 h

With 1H-imidazole; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500614

upstream raw materials:

tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane

(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)-hex-5-en-1-ol

methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside

methyl-2,3-di-O-benzyl-6-iodo-4-O-(4-methoxybenzyl)-6-deoxy-α-D-glucopyranoside

Downstream raw materials:

(E,2R,3S,4R,7R,8S,9R)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene-4,7-diol

(E,2S,3S,4R,7R,8S,9S)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)dec-5-ene-1,10-diol

(E,2S,3S,4R,7R,8S,9S)-2,3,4,7,8,9-hexa(benzyloxy)dec-5-ene-1,10-diol

(E,2R,3S,4R,7R,8S,9R)-4,7-bis(acetoxy)-2,3,8,9-tetra(benzyloxy)-1,10-bis(tert-butyldimethylsilyloxy)dec-5-ene