(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

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Chemical Name:(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol
CAS No.:400737-89-5
Molecular Formula:C₂₆H₃₈O₅SSi
Molecular Weight:490.736
Hs Code.:

Synonyms:(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

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Chemical Property of (2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

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Technology Process of (2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

There total 7 articles about (2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol 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: 92.0%

: 400737-85-1
[(2S,3S,4S,5R,6S)-4-Allyloxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane

: 400737-89-5
(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Guidance literature:: [(2S,3S,4S,5R,6S)-4-Allyloxy-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-yloxy]-tert-butyl-dimethyl-silane; With 1,4-diaza-bicyclo[2.2.2]octane; tris(triphenylphosphine)rhodium(I) chloride; In methanol; water; for 1h; Heating;

With osmium(VIII) oxide; N-methyl-2-indolinone; In water; acetone; at 25 ℃; for 12h;
DOI:10.1002/1521-3773(20011015)40:20<3849::AID-ANIE3849>3.0.CO;2-M

Reference yield:

: 131087-35-9
phenyl 2,3-O-isopropylidene-1-thio-α-L-rhamnopyranoside

: 400737-89-5
(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: 95 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: 92 percent / boron trichloride dimethylsulfide / CH₂Cl₂ / 0.5 h / 0 °C

3.1: nBu₂SnO / toluene / 6 h / Heating

3.2: 68 percent / cesium fluoride / dimethylformamide / 12 h / 70 °C

4.1: NaH / dimethylformamide / 25 °C

4.2: 83 percent / tetra-n-butylammonium iodide / dimethylformamide / 25 °C

5.1: (Ph₃P)3RhCl; 1,4-diazabicyclo[2.2.2]octane / methanol; H₂O / 2 h / Heating

5.2: 92 percent / N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; Wilkinson's catalyst; boron trichloride - methyl sulfide complex; sodium hydride; di(n-butyl)tin oxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja0304953

Reference yield:

: 331456-83-8
S-phenyl 2,3-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-1-thio-α-L-rhamnopyranoside

: 400737-89-5
(2S,3R,4S,5R,6S)-3-(tert-Butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-4-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: 92 percent / boron trichloride dimethylsulfide / CH₂Cl₂ / 0.5 h / 0 °C

2.1: nBu₂SnO / toluene / 6 h / Heating

2.2: 68 percent / cesium fluoride / dimethylformamide / 12 h / 70 °C

3.1: NaH / dimethylformamide / 25 °C

3.2: 83 percent / tetra-n-butylammonium iodide / dimethylformamide / 25 °C

4.1: (Ph₃P)3RhCl; 1,4-diazabicyclo[2.2.2]octane / methanol; H₂O / 2 h / Heating

4.2: 92 percent / N-methylmorpholine N-oxide; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 12 h / 25 °C

With 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; boron trichloride - methyl sulfide complex; sodium hydride; di(n-butyl)tin oxide; In methanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ja0304953