Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

Base Information

Chemical Name:Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester
CAS No.:592533-02-3
Molecular Formula:C₃₁H₃₄O₆S
Molecular Weight:534.673
Hs Code.:

Synonyms:Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

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Chemical Property of Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

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Technology Process of Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

There total 7 articles about Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] 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: 77.0%

: 592533-01-2
Thioacetic acid S-((2R,3R,4R,5S,6R)-6-allyl-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl) ester

: 592533-02-3
Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

Guidance literature:: Thioacetic acid S-((2R,3R,4R,5S,6R)-6-allyl-4,5-bis-benzyloxy-2-benzyloxymethyl-tetrahydro-pyran-3-yl) ester; With ozone; In dichloromethane; at -78 ℃; for 1h;

With zinc; In acetic acid; at 20 ℃;
DOI:10.1016/S0040-4039(03)01039-6

Reference yield:

: 53263-18-6,82659-53-8,98920-46-8,98920-48-0,98920-49-1,103773-87-1,98920-44-6
allyl 2,3,4,6-tetra-O-acetyl-α-D-galactopyranoside

: 592533-02-3
Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

Guidance literature:: Multi-step reaction with 7 steps

1.1: NaOMe / 2 h / 20 °C

2.1: TsOH / acetonitrile / 20 °C

3.1: 73 percent / NaH / dimethylformamide / 20 °C

4.1: 81 percent / NaCN*BH₃ / aq. HCl; tetrahydrofuran / 3 h / 0 - 20 °C

5.1: pyridine; CH₂Cl₂ / 3 h / 0 - 20 °C

6.1: dimethylformamide / 20 °C

7.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

7.2: 77 percent / Zn / acetic acid / 20 °C

With sodium methylate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; pyridine; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(03)01039-6

Reference yield:

: 133697-14-0
2,6-anhydro-7,8,9-trideoxy-D-glycero-L-galacto-non-8-enitol

: 592533-02-3
Thioacetic acid S-[(2R,3R,4R,5S,6R)-4,5-bis-benzyloxy-2-benzyloxymethyl-6-(2-oxo-ethyl)-tetrahydro-pyran-3-yl] ester

Guidance literature:: Multi-step reaction with 6 steps

1.1: TsOH / acetonitrile / 20 °C

2.1: 73 percent / NaH / dimethylformamide / 20 °C

3.1: 81 percent / NaCN*BH₃ / aq. HCl; tetrahydrofuran / 3 h / 0 - 20 °C

4.1: pyridine; CH₂Cl₂ / 3 h / 0 - 20 °C

5.1: dimethylformamide / 20 °C

6.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

6.2: 77 percent / Zn / acetic acid / 20 °C

With sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; ozone; In tetrahydrofuran; pyridine; hydrogenchloride; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0040-4039(03)01039-6