Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

Base Information

Chemical Name:Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester
CAS No.:142003-06-3
Molecular Formula:C₂₆H₂₉O₁₂PS
Molecular Weight:596.549
Hs Code.:

Synonyms:Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

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Chemical Property of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

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Technology Process of Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

There total 9 articles about Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-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:

: 28585-88-8
methyl 5-deoxy-5-thio-α-D-glucopiranoside

: 142003-06-3
Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

Guidance literature:: Multi-step reaction with 9 steps

1: 85 percent / p-TsOH / dimethylformamide / 1.5 h / 60 °C

2: 1.) NaH / 1.) DMF, 20 deg C, 4 h, 2.) DMF, 20 deg C, 20 h

3: 62 percent / NaBH₃CN, ethereal HCl / tetrahydrofuran / 3.5 h / Heating

4: 1.) (COCl)2, DMSO, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 1.5 h, 2.) CH₂Cl₂, -78 deg C, 5 min

5: 88 percent / NaBH₄ / benzene; ethanol / 0.13 h / 0 °C

6: Na, liquid NH₃ / tetrahydrofuran / 0.67 h / -78 °C

7: H₂SO₄, AcOH / 17 h / 20 °C

8: 56 percent / H₂NNH₂*AcOH / dimethylformamide / 0.5 h / 50 °C

9: 1.) nBuLi / 1.) THF, hexane, -70 deg C, 2 min, 2.) THF, hexane, from -70 to -60 deg C, 30 min

With hydrogenchloride; sodium tetrahydroborate; n-butyllithium; oxalyl dichloride; sulfuric acid; ammonia; sodium; hydrazinium monoacetate; sodium hydride; sodium cyanoborohydride; toluene-4-sulfonic acid; acetic acid; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; benzene;

Reference yield:

: 75686-37-2
methyl 5-thio-α-D-galactopyranoside

: 142003-06-3
Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

Guidance literature:: Multi-step reaction with 3 steps

1: H₂SO₄, AcOH / 17 h / 20 °C

2: 56 percent / H₂NNH₂*AcOH / dimethylformamide / 0.5 h / 50 °C

3: 1.) nBuLi / 1.) THF, hexane, -70 deg C, 2 min, 2.) THF, hexane, from -70 to -60 deg C, 30 min

With n-butyllithium; sulfuric acid; hydrazinium monoacetate; acetic acid; In N,N-dimethyl-formamide;

Reference yield:

: 72661-69-9
methyl 2,3,4,6-tetra-O-acetyl-5-thio-α-D-galactopyranoside

: 142003-06-3
Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-(diphenoxy-phosphoryloxy)-tetrahydro-thiopyran-3-yl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 56 percent / H₂NNH₂*AcOH / dimethylformamide / 0.5 h / 50 °C

2: 1.) nBuLi / 1.) THF, hexane, -70 deg C, 2 min, 2.) THF, hexane, from -70 to -60 deg C, 30 min

With n-butyllithium; hydrazinium monoacetate; In N,N-dimethyl-formamide;