S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

Base Information

Chemical Name:S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate
CAS No.:1416356-07-4
Molecular Formula:C₂₈H₃₈O₄SSi
Molecular Weight:498.759
Hs Code.:

Synonyms:S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

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Chemical Property of S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

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Technology Process of S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

There total 11 articles about S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate 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: 88.0%

: 994-30-9
triethylsilyl chloride

: 1416356-12-1
S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-3-hydroxy-5-methylenetetrahydropyran-2-carboxylate

: 1416356-07-4
S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

Guidance literature:: With 1H-imidazole; In N,N-dimethyl-formamide; at 50 ℃; for 46h;
DOI:10.1246/bcsj.20120152

Reference yield:

: C₂₁H₃₂O₅Si

: 106-45-6
para-thiocresol

: 1416356-07-4
S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

: 1416356-12-1
S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-3-hydroxy-5-methylenetetrahydropyran-2-carboxylate

Guidance literature:: With dmap; dicyclohexyl-carbodiimide; In dichloromethane; at 0 - 20 ℃; for 16h;
DOI:10.1246/bcsj.20120152

Reference yield:

: 1416356-29-0
C₂₇H₄₈O₄Si₂

: 1416356-07-4
S-(p-tolyl)(2S,3S,6R)-6-(benzyloxymethyl)-5-methylene-3-(triethylsilyloxy)tetrahydropyran-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1: pyridinium p-toluenesulfonate / dichloromethane; methanol / 0.17 h / -10 °C

2: triethylamine; sulfur trioxide pyridine complex; dimethyl sulfoxide / dichloromethane / 0.5 h / 0 °C

3: sodium chlorite; 2-methyl-but-2-ene; sodium dihydrogenphosphate / water; tert-butyl alcohol / 2 h / 0 - 20 °C

4: dicyclohexyl-carbodiimide; dmap / dichloromethane / 16 h / 0 - 20 °C

With dmap; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; sulfur trioxide pyridine complex; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; In methanol; dichloromethane; water; tert-butyl alcohol; 2: |Parikh-Doering Oxidation;
DOI:10.1246/bcsj.20120152