ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

Base Information

• Chemical Name: ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside
• CAS No.: 282107-57-7
• Molecular Formula: C₃₈H₄₆O₅SSi
• Molecular Weight: 642.932
• Mol file: 282107-57-7.mol

Synonyms:ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

Chemical Property of ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

There total 20 articles about ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside 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: 71.0%

p-Methoxybenzyl bromide (2746-25-0) + ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside (282107-64-6) → ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside (282107-57-7)

Guidance literature:

With 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In acetonitrile; at 0 - 20 ℃; for 2h;

DOI:10.1016/S0040-4039(00)01273-9

Reference yield:

ethyl 3-O-benzyl-1-thio-α-D-arabinofuranoside (282107-56-6) → ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside (282107-57-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 80 percent / imidazole / dimethylformamide / 3 h / 20 °C

2: 70 percent / BEMP / acetonitrile / 1 h / 20 °C

With 1H-imidazole; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1099-0690(200211)2002:22<3864::AID-EJOC3864>3.0.CO;2-8

Reference yield:

Ethyl 2-O-benzoyl-3-O-benzyl-1-thio-α-D-arabinofuranoside (282107-51-1) → ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-2-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside (282107-57-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 93 percent / imidazole / dimethylformamide / 1 h / 20 °C

2: 80 percent / MeONa / methanol / 20 °C

3: 70 percent / BEMP / acetonitrile / 1 h / 20 °C

With 1H-imidazole; sodium methylate; 2-tert-butylimino-2-diethylamino-1,3-dimethyl-perhydro-1,3,2-diazaphosphorine; In methanol; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1002/1099-0690(200211)2002:22<3864::AID-EJOC3864>3.0.CO;2-8

upstream raw materials:

p-Methoxybenzyl bromide

ethyl 3-O-benzyl-5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside

D-Arabinose

benzyl bromide

Downstream raw materials:

8-(methoxycarbonyl)octyl 2-O-(3-O-benzyl-5-O-tert-butyldiphenylsilyl)-β-D-arabinofuranosyl)-3-O-benzyl-5-O-pivaloyl-α-D-arabinofuranoside

9-[(2S,3S,4R,5R)-3-[(2S,3S,4R,5R)-3-Acetoxy-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-tetrahydro-furan-2-yloxy]-4-benzyloxy-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester

Benzoic acid (2S,3S,4R,5R)-4-benzyloxy-5-[(2R,3S,4R,5R)-4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-3-(4-methoxy-benzyloxy)-tetrahydro-furan-2-yloxymethyl]-2-octyloxy-tetrahydro-furan-3-yl ester

9-[4-benzyloxy-3-[[4-benzyloxy-5-(tert-butyl-diphenyl-silanyloxymethyl)-2-ethylsulfanyl-tetrahydro-furan-3-yloxy]-(4-methoxy-phenyl)-methoxy]-5-(2,2-dimethyl-propionyloxymethyl)-tetrahydro-furan-2-yloxy]-nonanoic acid methyl ester