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

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Chemical Name:(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol
CAS No.:256413-33-9
Molecular Formula:C₂₆H₃₈O₅SSi
Molecular Weight:490.736
Hs Code.:

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

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

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

There total 9 articles about (2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-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: 90.0%

: 256413-32-8
Toluene-4-sulfonic acid (2R,3S,4S,5R,6S)-5-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-4-(4-methoxy-benzyloxy)-6-phenylsulfanyl-tetrahydro-pyran-2-ylmethyl ester

: 256413-33-9
(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: With lithium aluminium tetrahydride; In tetrahydrofuran; at 45 ℃; for 3h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9

Reference yield:

: 71676-30-7,87508-17-6,138922-03-9,87508-18-7
phenyl 4,6-di-O-benzylidene-1-thio-β-D-galactopyranoside

: 256413-33-9
(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 5 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 87 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

3.1: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

4.1: 97 percent / pyridine / 12 h / 0 - 25 °C

5.1: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc trifluoromethanesulfonate; di(n-butyl)tin oxide; ethanethiol; In tetrahydrofuran; dichloromethane; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Ring cleavage / 4.1: Tosylation / 5.1: Reduction;
DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

: 179072-68-5
phenyl 4,6-O-benzylidene-3-O-(p-methoxybenzyl)-1-thio-β-D-galactopyranoside

: 256413-33-9
(2R,3S,4S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2-methyl-6-phenylsulfanyl-tetrahydro-pyran-3-ol

Guidance literature:: Multi-step reaction with 4 steps

1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

2: 77 percent / EtSH; Zn(OTf)2 / CH₂Cl₂ / 2 h / 0 °C

3: 97 percent / pyridine / 12 h / 0 - 25 °C

4: 90 percent / LAH / tetrahydrofuran / 3 h / 0 - 45 °C

With pyridine; 2,6-dimethylpyridine; lithium aluminium tetrahydride; zinc trifluoromethanesulfonate; ethanethiol; In tetrahydrofuran; dichloromethane; 1: Etherification / 2: Ring cleavage / 3: Tosylation / 4: Reduction;
DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L