[1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one

Base Information

• Chemical Name: [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one
• CAS No.: 783334-61-2
• Molecular Formula: C₂₇H₃₀O₁₁S
• Molecular Weight: 562.595

Synonyms:[1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one

Chemical Property of [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one

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Technology Process of [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one

There total 2 articles about [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one 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:

[3aR-(3aα,11α,12β,12aα)]-12-(acetyloxy)-3a,11,12,12a-tetrahydro-6-methoxy-2,2-dimethyl-11-(phenylthio)-5H-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-h][1]benzopyran-5-one (164106-86-9) → [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one (783334-61-2)

Guidance literature:

Multi-step reaction with 2 steps

1: TFA / tetrahydrofuran; H₂O / 2 h / Heating

2: 413 mg / diisopropylethylamine / CH₂Cl₂ / 2 h / Heating

With N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water;

DOI:10.1021/jo049153l

Reference yield:

chloromethyl methyl ether (107-30-2) + (1R,2R,3S,4R)-2,3,4-Trihydroxy-7-methoxy-1-phenylsulfanyl-1,2,3,4-tetrahydro-5,8,10-trioxa-cyclopenta[b]phenanthren-6-one → [1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one (783334-61-2)

Guidance literature:

With N-ethyl-N,N-diisopropylamine; In dichloromethane; for 2h; Heating;

DOI:10.1021/jo049153l

Reference yield: 73.0%

[1R-(1β,2α,3β,4β)]-6-methoxy2,3,4-tri(methoxymethyl)-1,2,3,4-tetrahydro-1-(phenylthio)-2H-[1,3]benzodioxolo[5,6-c]-[1]benzopyran-6-one (783334-61-2) → 4-methoxy-6-[(3S,4R,5R)(3,4,5-tris-methoxymethoxy-6-oxocyclohex-1-enyl)]benzo[1,3]dioxole-5-carboxamide

Guidance literature:

With ammonia; In methanol; at 0 - 20 ℃; for 4h;

DOI:10.1021/jo049153l

upstream raw materials:

chloromethyl methyl ether

[3aR-(3aα,11α,12β,12aα)]-12-(acetyloxy)-3a,11,12,12a-tetrahydro-6-methoxy-2,2-dimethyl-11-(phenylthio)-5H-[1,3]benzodioxolo[5,6-c]-1,3-dioxolo[4,5-h][1]benzopyran-5-one

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