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

Base Information

• Chemical Name: 2,5-didesoxy-2-C-methyl-3-O-benzyl-D-arabinose trimethylenedithioacetal
• CAS No.: 110595-02-3
• Molecular Formula: C₁₆H₂₄O₂S₂
• Molecular Weight: 312.497
• Mol file: 110595-02-3.mol

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

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

There total 4 articles about 2,5-didesoxy-2-C-methyl-3-O-benzyl-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: 91.0%

1.3-propanedithiol (109-80-8) + methyl-2,5-didesoxy-2-C-methyl-3-O-benzyl-α-D-arabinofuranoside (93215-29-3) → 2,5-didesoxy-2-C-methyl-3-O-benzyl-D-arabinose trimethylenedithioacetal (110595-02-3)

Guidance literature:

With zinc(II) chloride; at 0 ℃; for 0.5h;

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-D-arabinose trimethylenedithioacetal (110595-02-3)

Guidance literature:

Multi-step reaction with 4 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

With 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-D-arabinose trimethylenedithioacetal (110595-02-3)

Guidance literature:

Multi-step reaction with 3 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

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

DOI:10.1007/BF00953355

upstream raw materials:

1.3-propanedithiol

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

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

Downstream raw materials:

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