Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester
CAS No.:157219-89-1
Molecular Formula:C₂₂H₂₈O₇S
Molecular Weight:436.526
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

There total 5 articles about Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester 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:

: 75837-45-5
methyl 3-O-benzyl-2-deoxy-2-C-methyl-α-D-altropyranoside

: 98-59-9
p-toluenesulfonyl chloride

: 157219-89-1
Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With dmap; triethylamine; In dichloromethane; at 0 ℃;
DOI:10.1021/jo00083a008

Reference yield:

: 109958-35-2
(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 157219-89-1
Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

With dmap; toluene-4-sulfonic acid; triethylamine; In methanol; dichloromethane; 1: Hydrolysis / 2: Tosylation;
DOI:10.1021/jo990988j

Reference yield:

: 68907-47-1
methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

: 157219-89-1
Toluene-4-sulfonic acid (2R,3S,4S,5S,6S)-4-benzyloxy-3-hydroxy-6-methoxy-5-methyl-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

With dmap; tetra-(n-butyl)ammonium iodide; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; 1: Alkylation / 2: Hydrolysis / 3: Tosylation;
DOI:10.1021/jo990988j