tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane
• CAS No.: 256342-23-1
• Molecular Formula: C₂₉H₄₂O₆SSi
• Molecular Weight: 546.8

Synonyms:tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane

Chemical Property of tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane

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Technology Process of tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane

There total 3 articles about tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-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: 95.0%

p-methoxybenzyl chloride (824-94-2) + (3aS,4R,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol (256341-88-5) → tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane (256342-23-1)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 4h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane (256342-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: NaH / dimethylformamide; tetrahydrofuran / 0.25 h / 0 °C

2.2: 95 percent / nBu₄NI / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

With 2,6-dimethylpyridine; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Metallation / 2.2: Etherification;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside (126092-08-8) → tert-Butyl-[(3aS,4R,6R,7R,7aS)-7-(4-methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-ylmethoxy]-dimethyl-silane (256342-23-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -78 °C

2.1: NaH / dimethylformamide; tetrahydrofuran / 0.25 h / 0 °C

2.2: 95 percent / nBu₄NI / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

With 2,6-dimethylpyridine; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Metallation / 2.2: Etherification;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

p-methoxybenzyl chloride

(3aS,4R,6R,7R,7aS)-6-(tert-Butyl-dimethyl-silanyloxymethyl)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

t-butyldimethylsiyl triflate

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

Downstream raw materials:

C₅₅H₇₆O₁₄SeSi

C₅₆H₇₄O₁₆Si

C₄₉H₆₈O₁₇SSi

C₄₉H₇₀O₁₅Si

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