(3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole

Base Information

• Chemical Name: (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole
• CAS No.: 454475-03-7
• Molecular Formula: C₂₃H₂₈O₅S
• Molecular Weight: 416.538

Synonyms:(3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole

Chemical Property of (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole

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Technology Process of (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole

There total 2 articles about (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole 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:

p-methoxybenzyl chloride (824-94-2) + phenyl 2,3-O-isopropylidene-1-thio-L-rhamnofuranoside (454474-74-9) → (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole (454475-03-7)

Guidance literature:

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

DOI:10.1016/S0040-4039(98)02440-X

Reference yield:

phenyl 5-O-acetyl-2,3-O-isopropylidene-1-thio-L-rhamnofuranoside → (3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole (454475-03-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / sodium methoxide / methanol / 16 h / 20 °C

2: NaH; n-Bu₄NI / dimethylformamide; various solvent(s) / 19 h / 0 °C

With sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jo020211h

Reference yield:

(3aR,4S,6aR)-4-[(S)-1-(4-Methoxy-benzyloxy)-ethyl]-2,2-dimethyl-6-phenylsulfanyl-tetrahydro-furo[3,4-d][1,3]dioxole (454475-03-7) → 2,3-O-isopropylidene-5-O-p-methoxybenzyl-L-rhamnofuranose (454474-75-0)

Guidance literature:

With N-Bromosuccinimide; In tetrahydrofuran; water; at 0 ℃; Yield given;

DOI:10.1016/S0040-4039(98)02440-X

upstream raw materials:

p-methoxybenzyl chloride

phenyl 2,3-O-isopropylidene-1-thio-L-rhamnofuranoside

Downstream raw materials:

2,3-O-isopropylidene-5-O-p-methoxybenzyl-L-rhamnofuranose

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