methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside

Base Information

• Chemical Name: methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside
• CAS No.: 158513-63-4
• Molecular Formula: C₁₆H₂₂O₄S
• Molecular Weight: 310.414
• Mol file: 158513-63-4.mol

Synonyms:methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside

Chemical Property of methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside

There total 4 articles about methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside 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: 81.0%

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside (4137-56-8) + phenylmethanethiol (100-53-8) → methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside (158513-63-4)

Guidance literature:

With sodium methylate; In N,N-dimethyl-formamide; at 90 ℃; for 5h;

DOI:10.1016/j.carres.2008.08.010

Reference yield: 7.0%

methyl 5-deoxy-2,3-O-isopropylidene-5-thiocyanato-β-D-ribofuranoside (158420-07-6) + benzylmagnesium chloride (6921-34-2) → methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside (158513-63-4)

Guidance literature:

In tetrahydrofuran; diethyl ether; at -40 ℃; for 0.333333h;

DOI:10.1016/S0040-4020(01)87009-5

Reference yield:

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside (4137-56-8) → methyl 5-S-benzyl-2,3-O-isopropylidene-5-thio-β-D-ribofuranoside (158513-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 91 percent / dimethylformamide / 6 h / 120 - 130 °C

2: 7 percent / diethyl ether; tetrahydrofuran / 0.33 h / -40 °C

In tetrahydrofuran; diethyl ether; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87009-5

upstream raw materials:

methyl 5-deoxy-2,3-O-isopropylidene-5-thiocyanato-β-D-ribofuranoside

benzylmagnesium chloride

methyl 2,3-O-isopropylidene-5-O-p-tolylsulfonyl-β-D-ribofuranoside

phenylmethanethiol

Downstream raw materials:

methyl 5-benzylsulfonyl-5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside