2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal

Base Information

• Chemical Name: 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal
• CAS No.: 110595-03-4
• Molecular Formula: C₂₃H₂₈O₃S₂
• Molecular Weight: 416.606
• Mol file: 110595-03-4.mol

Synonyms:2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal

Chemical Property of 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal

There total 5 articles about 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal 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: 70.5%

benzoyl chloride (98-88-4) + 2,5-didesoxy-2-C-methyl-3-O-benzyl-D-arabinose trimethylenedithioacetal (110595-02-3) → 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal (110595-03-4)

Guidance literature:

With pyridine; at 0 ℃; for 12h;

DOI:10.1007/BF00953355

Reference yield:

(1R,4R,5R)-2-Methoxy-4-methyl-3,6-dioxa-bicyclo[3.1.0]hexane → 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal (110595-03-4)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) n-BuLi / 1.) THF, hexane, 4 h, 2.) THF, -15 deg C, 20 h

2: 1.) NaCH₂SOCH₃ / 1.) DMSO, 0.5 h, 2.) 1 h

3: 94 percent / skeletal nickel / acetone / 13 h / Heating

4: 91 percent / ZnCl₂ / 0.5 h / 0 °C

5: 70.5 percent / pyridine / 12 h / 0 °C

With pyridine; n-butyllithium; nickel; sodium methylsulfinylmethanide; zinc(II) chloride; In acetone;

DOI:10.1007/BF00953355

Reference yield:

methyl-2,5-didesoxy-2-C-(1,3-dithian-2-yl)-α-D-arabinofuranoside (110595-00-1) → 2,5-didesoxy-2-C-methyl-3-O-benzyl-4-O-benzoyl-D-arabinose trimethylenedithioacetal (110595-03-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 1.) NaCH₂SOCH₃ / 1.) DMSO, 0.5 h, 2.) 1 h

2: 94 percent / skeletal nickel / acetone / 13 h / Heating

3: 91 percent / ZnCl₂ / 0.5 h / 0 °C

4: 70.5 percent / pyridine / 12 h / 0 °C

With pyridine; nickel; sodium methylsulfinylmethanide; zinc(II) chloride; In acetone;

DOI:10.1007/BF00953355

upstream raw materials:

benzoyl chloride

2,5-didesoxy-2-C-methyl-3-O-benzyl-D-arabinose trimethylenedithioacetal

methyl-2,5-didesoxy-2-C-methyl-3-O-benzyl-α-D-arabinofuranoside

methyl-2,5-didesoxy-2-C-(1,3-dithian-2-yl)-α-D-arabinofuranoside