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

Base Information

Chemical Name:(2R,3R,4R,5S,6R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran
CAS No.:256327-56-7
Molecular Formula:C₃₂H₅₂O₅SSi₂
Molecular Weight:604.999
Hs Code.:

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

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

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

There total 7 articles about (2R,3R,4R,5S,6R)-3,4-Bis-(tert-butyl-dimethyl-silanyloxy)-5-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-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: 93.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 256327-55-6
(2R,3S,4S,5S,6R)-5-(4-Methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3,4-diol

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

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 0.5h;
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:

: 151669-25-9
Phenyl 2,3-O-isopropylidene-6-O-(p-toluenesulfonyl)-1-thio-α-D-mannopyranoside

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

Guidance literature:: Multi-step reaction with 6 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

With 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; 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;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4

Reference yield:

: 126092-08-8
phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

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

Guidance literature:: Multi-step reaction with 7 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

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; ethylene glycol; 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;
DOI:10.1002/1521-3765(20000901)6:17<3095::AID-CHEM3095>3.0.CO;2-4