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

Base Information

• Chemical Name: 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
• CAS No.: 256413-55-5
• Molecular Formula: C₃₃H₄₂O₆SSi
• Molecular Weight: 594.844
• Mol file: 256413-55-5.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 4 articles about 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 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%

t-butyldimethylsiyl triflate (69739-34-0) + phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9) → 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 (256413-55-5)

Guidance literature:

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

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:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → 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 (256413-55-5)

Guidance literature:

Multi-step reaction with 2 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

With 2,6-dimethylpyridine; di(n-butyl)tin oxide; In dichloromethane; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification;

DOI:10.1002/1521-3765(20000901)6:17<3149::AID-CHEM3149>3.0.CO;2-L

Reference yield:

p-methoxybenzyl chloride (824-94-2) → 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 (256413-55-5)

Guidance literature:

Multi-step reaction with 2 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

With 2,6-dimethylpyridine; di(n-butyl)tin oxide; In dichloromethane; toluene; 1.1: Cyclization / 1.2: Ring cleavage / 2.1: Etherification;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3345::AID-ANIE3345>3.0.CO;2-9

upstream raw materials:

t-butyldimethylsiyl triflate

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

p-methoxybenzyl chloride

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

7-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

toluene-4-sulfonic acid 5-(tert-butyl-dimethyl-silanyloxy)-6-[3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-3,4-dihydroxy-4-methyl-tetrahydro-pyran-2-ylmethyl ester

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

(2R,4aR,6S,7S,8S,8aR)-7-(tert-Butyl-dimethyl-silanyloxy)-6-[(2S,3R,4S,5S,6R)-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methyl-2-triisopropylsilanyloxy-tetrahydro-pyran-4-yloxy]-8-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-8-ol