(2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol
• CAS No.: 256327-57-8
• Molecular Formula: C₂₄H₄₄O₄SSi₂
• Molecular Weight: 484.848

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

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

Chemical Property:

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

There total 10 articles about (2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-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: 91.0%

(2R,3R,4R,5S,6R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran (256327-56-7) → (2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256327-57-8)

Guidance literature:

With water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; at 0 - 25 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3334::AID-ANIE3334>3.0.CO;2-H DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside (151669-25-9) → (2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256327-57-8)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 36.65 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

2.1: 90 percent / LAH / tetrahydrofuran / 6 h / 0 - 45 °C

3.1: 80 percent / TsOH; (CH₂OH)2 / methanol / 10 h / 25 °C

4.1: nBu₂SnO / toluene / 3 h / Heating

4.2: 83 percent / nBu₄NI / toluene / 3 h / 25 - 110 °C

5.1: 91 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

6.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

7.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; water; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Etherification / 2.1: Reduction / 3.1: Ring cleavage / 4.1: Cyclization / 4.2: Ring cleavage / 5.1: Silyl ether cleavage / 6.1: Etherification / 7.1: Oxidation;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside (126092-08-8) → (2R,3S,4R,5R,6R)-4,5-Bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-2-phenylsulfanyl-tetrahydro-pyran-3-ol (256327-57-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / 12 h / 0 - 25 °C

2.1: 36.65 g / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 90 percent / LAH / tetrahydrofuran / 6 h / 0 - 45 °C

4.1: 80 percent / TsOH; (CH₂OH)2 / methanol / 10 h / 25 °C

5.1: nBu₂SnO / toluene / 3 h / Heating

5.2: 83 percent / nBu₄NI / toluene / 3 h / 25 - 110 °C

6.1: 91 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

7.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

8.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; water; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene; 1.1: Tosylation / 2.1: Etherification / 3.1: Reduction / 4.1: Ring cleavage / 5.1: Cyclization / 5.2: Ring cleavage / 6.1: Silyl ether cleavage / 7.1: Etherification / 8.1: Oxidation;

DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

upstream raw materials:

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

t-butyldimethylsiyl triflate

Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

(2R,3R,4S,5R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-6-fluoro-2-methyl-5-phenylsulfanyl-tetrahydro-pyran

(2R,3S,4R,6S)-6-[(2R,3R,4S,5R)-4-Benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3,4-diol

(2R,3R,4R,6S)-4-Allyloxy-6-[(2R,3R,4S,5R)-4-benzyloxy-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran-3-yloxy]-2-methyl-tetrahydro-pyran-3-ol

(2R,3R,4S,5R)-4-Benzyloxy-3-[(2S,4R,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-5,6-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-pyran

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