benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside

Base Information

• Chemical Name: benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside
• CAS No.: 136737-52-5
• Molecular Formula: C₂₆H₂₈O₂S₂
• Molecular Weight: 436.639
• Mol file: 136737-52-5.mol

Synonyms:benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside

Chemical Property of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside

There total 6 articles about benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside 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: 85.0%

3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal (136737-51-4) → benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside (136737-52-5)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; barium carbonate; In 1,4-dioxane; for 2.5h; Heating;

DOI:10.1002/1099-0690(200103)2001:6<1077::AID-EJOC1077>3.0.CO;2-0

Reference yield: 66.0%

3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal (134700-11-1) → benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside (136737-52-5)

Guidance literature:

With 1H-imidazole; iodine; triphenylphosphine; In toluene;

DOI:10.1080/15257779508012449

Reference yield:

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside (132487-16-2) → benzyl 3,5-di-O-benzyl-2-deoxy-1,4-dithio-α-threo-L-threo-pentofuranoside (136737-52-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 85 percent / aq. HCl

2.1: methanesulfonyl chloride; pyridine

2.2: 40 percent / NaI; BaCO₃ / acetone

With pyridine; hydrogenchloride; methanesulfonyl chloride;

DOI:10.1016/j.carres.2005.07.011

upstream raw materials:

3,5-di-O-benzyl-2-deoxy-4-O-methanesulphonyl-D-erythro-pentose dibenzyl dithioacetal

3,4-di-O-benzyl-2-deoxy-D-erythro-pentose bisbenzyl dithioacetal

methyl 3,5-di-O-benzyl-2-deoxy-D-ribofuranoside

phenylmethanethiol

Downstream raw materials:

(2S,3S)-5-Benzylsulfanyl-2-hydroxymethyl-tetrahydro-thiophen-3-ol

(2S,3S)-3-Benzyloxy-2-benzyloxymethyl-2,3-dihydro-thiophene

1-O-acetyl-3,5-di-O-benzyl-2-deoxy-4-thio-α,L-threo-pentofuranose

1-(3,5-O-dibenzyl-2-deoxy-4-thio-β-L-threo-pentofuranosyl)-5-iodouracil