[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

Base Information

Chemical Name:[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane
CAS No.:256413-29-3
Molecular Formula:C₃₃H₄₂O₇SSi
Molecular Weight:610.844
Hs Code.:

Synonyms:[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

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Chemical Property of [(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

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Technology Process of [(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

There total 4 articles about [(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane 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%

: 256413-55-5
tert-Butyl-[(2R,4aR,6R,7S,8S,8aR)-8-(4-methoxy-benzyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

: 256413-29-3
[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at -20 - 0 ℃; for 2h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9 DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

: 159407-19-9
phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 256413-29-3
[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: nBu₂SnO / toluene / 3 h / Heating

1.2: 83 percent / nBu₄NI / 2 h / 25 - 110 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 92 percent / mCPBA / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-dimethylpyridine; di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Oxidation;
DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

: 824-94-2
p-methoxybenzyl chloride

: 256413-29-3
[(2R,4aR,6R,7S,8S,8aR)-6-Benzenesulfinyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

Guidance literature:: Multi-step reaction with 3 steps

1.1: Bu₂SnO / toluene / 3 h / 110 °C

1.2: 83 percent / Bu₄NI / toluene / 25 - 110 °C

2.1: 93 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / 0 - 25 °C

3.1: 92 percent / mCPBA / CH₂Cl₂ / 2 h / -20 - 0 °C

With 2,6-dimethylpyridine; di(n-butyl)tin oxide; 3-chloro-benzenecarboperoxoic acid; In dichloromethane; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification / 3.1: Oxidation;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9