(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Base Information

Chemical Name:(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran
CAS No.:256341-90-9
Molecular Formula:C₂₄H₃₀O₆S
Molecular Weight:446.565
Hs Code.:

Synonyms:(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Chemical Property of (3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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Technology Process of (3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

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

: 256341-89-6
[(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yl]-methanol

: 74-88-4
methyl iodide

: 256341-90-9
(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 0 - 25 ℃; for 1h;
DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2

Reference yield:

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

: 256341-90-9
(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 4 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

3.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

4.1: NaH / dimethylformamide / 0.25 h / 0 °C

4.2: 95 percent / dimethylformamide / 1 h / 0 - 25 °C

With 2,6-dimethylpyridine; tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Etherification / 2.1: Metallation / 2.2: Etherification / 3.1: Silyl ether cleavage / 4.1: Metallation / 4.2: Methylation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

: 256341-88-5
(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

: 256341-90-9
(3aS,4R,6R,7R,7aS)-7-(4-Methoxy-benzyloxy)-6-methoxymethyl-2,2-dimethyl-4-phenylsulfanyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran

Guidance literature:: Multi-step reaction with 3 steps

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

1.2: 95 percent / nBu₄NI / dimethylformamide; tetrahydrofuran / 4 h / 0 - 25 °C

2.1: 95 percent / TBAF / tetrahydrofuran / 1 h / 25 °C

3.1: NaH / dimethylformamide / 0.25 h / 0 °C

3.2: 95 percent / dimethylformamide / 1 h / 0 - 25 °C

With tetrabutyl ammonium fluoride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; 1.1: Metallation / 1.2: Etherification / 2.1: Silyl ether cleavage / 3.1: Metallation / 3.2: Methylation;
DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8