Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Name:Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester
CAS No.:176738-40-2
Molecular Formula:C₁₆H₂₄O₇S
Molecular Weight:360.428
Hs Code.:

Synonyms:Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-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: 99.0%

: 176738-39-9
toluene-4-sulfonic acid (2'R,3'S)-3'-allyloxytetrahydropyran-2'-ylmethyl ester

: 176738-40-2
Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With osmium(VIII) oxide; N-methyl-2-indolinone; In tetrahydrofuran; water; at 25 ℃; for 4h;
DOI:10.1016/0040-4039(96)00408-X

Reference yield:

: 125901-90-8
(2R,3S)-2-(hydroxymethyl)-3,6-dihydro-2H-pyran-3-ol

: 176738-40-2
Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

2: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

3: 93 percent / NaH, nBu₄NI / dimethylformamide / 10 h / 0 °C

4: 99 percent / OsO₄, NMO / tetrahydrofuran; H₂O / 4 h / 25 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00408-X

Reference yield:

: 149342-25-6,92131-91-4
((2R,3S)-3-acetoxy-3,6-dihydro-2H-pyran-2-yl)methyl acetate

: 176738-40-2
Toluene-4-sulfonic acid (2R,3S)-3-(2,3-dihydroxy-propoxy)-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 100 percent / NaOMe / methanol / 0.5 h

2: 99 percent / hydrogen / 10percent Pd/C / methanol / 8 h

3: 77 percent / Et₃N, DMAP / CH₂Cl₂ / 8 h / 0 °C

4: 93 percent / NaH, nBu₄NI / dimethylformamide / 10 h / 0 °C

5: 99 percent / OsO₄, NMO / tetrahydrofuran; H₂O / 4 h / 25 °C

With dmap; osmium(VIII) oxide; N-methyl-2-indolinone; hydrogen; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1016/0040-4039(96)00408-X