2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside

Base Information

• Chemical Name: 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside
• CAS No.: 920281-46-5
• Molecular Formula: C₂₆H₂₈O₄S
• Molecular Weight: 436.572
• Mol file: 920281-46-5.mol

Synonyms:2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside

Chemical Property of 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside

There total 7 articles about 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-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:

p-tolyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside (917590-91-1) → 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside (920281-46-5)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)01133-9

Reference yield:

p-cresyl 5-O-tert-butyldiphenylsilyl-1-thio-α-D-arabinofuranoside (204918-55-8) → 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside (920281-46-5)

Guidance literature:

Multi-step reaction with 2 steps

1: 98 percent / NaH / dimethylformamide / 2 h / 20 °C

2: 7.25 g / TBAF / tetrahydrofuran / 20 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide;

DOI:10.1021/ol062198j

Reference yield:

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose (845868-93-1) → 2,3-di-O-benzyl-1-(p-tolylthio)-1-deoxy-α-D-arabinofuranoside (920281-46-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 86 percent / BF₃*OEt₂ / CH₂Cl₂ / 0.5 h / 0 °C

2: 100 percent / NaOMe / methanol / 0.25 h / 20 °C

3: 98 percent / NaH / dimethylformamide / 2 h / 20 °C

4: 7.25 g / TBAF / tetrahydrofuran / 20 °C

With boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; sodium methylate; sodium hydride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/ol062198j

upstream raw materials:

p-tolyl 2,3-di-O-benzyl-5-O-(tert-butyldiphenylsilyl)-1-thio-α-D-arabinofuranoside

1,2,3-tri-O-acetyl-5-O-t-butyldiphenylsilyl-D-arabinofuranose

p-tolyl 5-O-t-butyldiphenylsilyl-2,3-di-O-acetyl-1-thio-α-D-arabinofuranoside

benzyl bromide

Downstream raw materials:

Benzoic acid (2R,3R,4S,5R)-3,4-bis-benzyloxy-5-p-tolylsulfanyl-tetrahydro-furan-2-ylmethyl ester

p-tolyl 2,3-O-dibenzyl-5-O-(4-methoxybenzyl)-1-thio-α-D-arabinofuranoside

p-tolyl 2,3-di-O-benzyl-5-O-tert-butyldimethylsilyl-1-thio-α-D-arabinofuranoside

p-tolyl 5-O-allyl-2,3-di-O-benzyl-1-thio-α-D-arabinofuranoside