(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

Base Information

Chemical Name:(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran
CAS No.:335197-23-4
Molecular Formula:C₂₅H₃₂O₇S
Molecular Weight:476.591
Hs Code.:

Synonyms:(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

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Chemical Property of (2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

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Technology Process of (2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

There total 5 articles about (2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]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: 98.0%

: 824-94-2
p-methoxybenzyl chloride

: 335197-22-3
(S)-1,2-O-(1-ethylthioethylidene)-α-D-xylopyranose

: 335197-23-4
(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

Guidance literature:: (S)-1,2-O-(1-ethylthioethylidene)-α-D-xylopyranose; With sodium hydride; In tetrahydrofuran; at 25 ℃; for 0.166667h;

p-methoxybenzyl chloride; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; for 4h; Further stages.; Heating;
DOI:10.1021/ja004098t

Reference yield:

: 62446-93-9
1,2,3,4-tetra-O-acetyl-D-xylopyranose

: 335197-23-4
(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

Guidance literature:: Multi-step reaction with 4 steps

1.1: 93 percent / HBr; AcOH / CH₂Cl₂ / 4 h / 0 - 25 °C

2.1: 82 percent / 2,6-lutidine / nitromethane / 12 h / 25 °C

3.1: NaOMe / methanol / 3 h / 25 °C

4.1: NaH / tetrahydrofuran / 0 °C

4.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating

With 2,6-dimethylpyridine; hydrogen bromide; sodium methylate; sodium hydride; acetic acid; In tetrahydrofuran; methanol; nitromethane; dichloromethane;
DOI:10.1021/ja012119t

Reference yield:

: 335197-21-2
Acetic acid (2S,3aR,6R,7S,7aR)-6-acetoxy-2-ethylsulfanyl-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran-7-yl ester

: 335197-23-4
(2S,3aR,6R,7S,7aR)-2-Ethylsulfanyl-6,7-bis-(4-methoxy-benzyloxy)-2-methyl-tetrahydro-[1,3]dioxolo[4,5-b]pyran

Guidance literature:: Multi-step reaction with 2 steps

1.1: NaOMe / methanol / 3 h / 25 °C

2.1: NaH / tetrahydrofuran / 0 °C

2.2: 5.14 g / tetrabutylammonium chloride / tetrahydrofuran / 4 h / Heating

With sodium methylate; sodium hydride; In tetrahydrofuran; methanol;
DOI:10.1021/ja012119t