(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

Base Information

Chemical Name:(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran
CAS No.:78462-73-4
Molecular Formula:C₂₃H₃₀O₆S
Molecular Weight:434.554
Hs Code.:

Synonyms:(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

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Chemical Property of (2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

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Technology Process of (2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

There total 1 articles about (2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran 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:

: 917-54-4
methyllithium

: 78462-71-2,78462-72-3
[(Z)-1-Benzenesulfonyl-2-((2S,4R,5S,6S)-4-benzyloxy-5,6-dimethoxy-tetrahydro-pyran-2-yl)-vinyl]-trimethyl-silane

: 78462-73-4
(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

Guidance literature:: With potassium fluoride; Yield given. Multistep reaction; 1.) THF, -78 deg C, 2.) methanol;
DOI:10.1246/cl.1981.457

Reference yield:

: 78462-73-4
(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

: (E)-(2R,5S,6R)-7-Benzenesulfonyl-2,3,3-trimethoxy-6,8-dimethyl-undec-9-ene-1,5-diol

Guidance literature:: Multi-step reaction with 9 steps

1: 97.5 percent / H₂, AcOH / Pd-black / ethanol / 48 h / Heating

2: 40 g / PPTS / CH₂Cl₂ / 5 h / Ambient temperature

3: 1.) n-BuLi / 1.) THF, HMPA, -78 deg C -> -40 deg C, 20 min; 2.) THF, HMPA, -20 deg C, 2 h

4: 53 g / trimethyl orthoformate, dl-10-camphorsulfonic acid / 12 h / 60 °C

5: 52.4 g / CrO₃-2Py / CH₂Cl₂ / 0.5 h / Ambient temperature

6: 43.4 g / dl-10-camphorsulfonic acid / methanol / 12 h / Ambient temperature

7: 44.9 g / tetrahydrofuran / Ambient temperature

8: 45.7 g / MCPBA / CH₂Cl₂ / 1 h / 0 °C

9: 40.3 g / NaBH₄ / ethanol; tetrahydrofuran / 1.5 h / Heating

With sodium tetrahydroborate; n-butyllithium; camphor-10-sulfonic acid; hydrogen; pyridinium p-toluenesulfonate; dipyridine chromium trioxide; acetic acid; 3-chloro-benzenecarboperoxoic acid; trimethyl orthoformate; palladium; In tetrahydrofuran; methanol; ethanol; dichloromethane;
DOI:10.1021/ja00323a032

Reference yield:

: 78462-73-4
(2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-4-benzyloxy-2,3-dimethoxy-tetrahydro-pyran

: (2S,3S,4R,6S)-6-((R)-2-Benzenesulfonyl-1-methyl-ethyl)-2,3-dimethoxy-4-(tetrahydro-pyran-2-yloxy)-tetrahydro-pyran

Guidance literature:: Multi-step reaction with 2 steps

1: 97.5 percent / H₂, AcOH / Pd-black / ethanol / 48 h / Heating

2: 40 g / PPTS / CH₂Cl₂ / 5 h / Ambient temperature

With hydrogen; pyridinium p-toluenesulfonate; acetic acid; palladium; In ethanol; dichloromethane;
DOI:10.1021/ja00323a032