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

Base Information

• Chemical Name: tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane
• CAS No.: 883972-86-9
• Molecular Formula: C₃₄H₄₆O₅Si
• Molecular Weight: 562.822
• Mol file: 883972-86-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 4 articles about tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane 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: 69.0%

(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)-hex-5-en-1-ol (883972-84-7) + tert-butyldimethylsilyl chloride (18162-48-6) → tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane (883972-86-9)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500614

Reference yield:

(2R,3S,4R)-2,3-Bis-benzyloxy-4-(4-methoxy-benzyloxy)-hex-5-enal → tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane (883972-86-9)

Guidance literature:

Multi-step reaction with 2 steps

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

2: 69 percent / imidazole / dimethylformamide

With 1H-imidazole; lithium aluminium tetrahydride; In diethyl ether; N,N-dimethyl-formamide;

DOI:10.1002/ejoc.200500614

Reference yield:

methyl 2,3-bis-O-benzyl-4-O-[(4-methoxyphenyl)methyl]-α-D-glucopyranoside (90633-95-7,94827-31-3,90633-90-2) → tert-butyl-[(2S,3S,4R)-2,3-bis(benzyloxy)-4-(4-methoxybenzyloxy)hex-5-enyloxy]dimethylsilane (883972-86-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 94 percent / PPh₃; I₂; imidazole / toluene

2: Zn; NH₄Cl / tetrahydrofuran; H₂O / 50 °C

3: 544 mg / LiAlH₄ / diethyl ether / 1.5 h / 0 - 20 °C

4: 69 percent / imidazole / dimethylformamide

With 1H-imidazole; lithium aluminium tetrahydride; iodine; ammonium chloride; triphenylphosphine; zinc; In tetrahydrofuran; diethyl ether; water; N,N-dimethyl-formamide; toluene;

DOI:10.1002/ejoc.200500614

upstream raw materials:

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

tert-butyldimethylsilyl chloride

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,2S,3S,4R,7R,8S,9S,12'R)-2,3,4,7,8,9-hexa(benzyloxy)-10-hydroxydec-5-enyl 12-hydroxystearate

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

(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

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