methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate

Base Information

• Chemical Name: methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate
• CAS No.: 271584-68-0
• Molecular Formula: C₁₈H₂₄O₈S
• Molecular Weight: 400.45

Synonyms:methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate

Chemical Property of methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate

Chemical Property:

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Technology Process of methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate

There total 2 articles about methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate 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: 89.0%

methyl [(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]acetate (55036-19-6) + p-toluenesulfonyl chloride (98-59-9) → methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate (271584-68-0)

Guidance literature:

With pyridine; at 20 ℃; for 20h;

DOI:10.1134/S1070428006110169

Reference yield:

2,3-O-isopropylidene-D-ribofuranose (67814-68-0,70266-87-4,76249-50-8,76249-51-9,93451-15-1,4099-88-1) → methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate (271584-68-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 76.7 percent / benzene / 2 h / 80 °C

2: 89 percent / pyridine / 20 h / 20 °C

With pyridine; In benzene;

DOI:10.1134/S1070428006110169

Reference yield:

2-mercaptophenylethane (4410-99-5) + methyl (2S,3S,4R,5R)-3,4-isopropylidenedioxy-5-toluenesulfonylmethyl-2-tetrahydrofurfurylacetate (271584-68-0) → ((3aS,4S,6S,6aS)-2,2-Dimethyl-6-phenethylsulfanylmethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester (271585-00-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 20 ℃; for 6h;

DOI:10.1016/S0960-894X(00)00021-4

upstream raw materials:

methyl [(3aS,4S,6R,6aR)-6-(hydroxymethyl)-2,2-dimethyltetrahydrofuro[3,4-d][1,3]dioxol-4-yl]acetate

p-toluenesulfonyl chloride

2,3-O-isopropylidene-D-ribofuranose

Downstream raw materials:

((3aS,4S,6S,6aS)-2,2-Dimethyl-6-phenethylsulfanylmethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester

((3aS,4S,6S,6aS)-2,2-Dimethyl-6-phenylsulfanylmethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester

((3aS,4S,6S,6aS)-6-Benzylsulfanylmethyl-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl)-acetic acid methyl ester

[(3aS,4S,6S,6aS)-6-(4-Chloro-phenylsulfanylmethyl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-acetic acid methyl ester

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