Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

Base Information

• Chemical Name: Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester
• CAS No.: 359436-35-4
• Molecular Formula: C₂₅H₃₃NO₅S₂
• Molecular Weight: 491.673

Synonyms:Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

Chemical Property of Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

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Technology Process of Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester

There total 4 articles about Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester 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%

carbon disulfide (75-15-0,12122-00-8) + (2-Cyclopentylidene-ethyl)-((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid benzyl ester (359436-34-3) + methyl iodide (74-88-4) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (359436-35-4)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at -30 - 0 ℃;

DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

(2-chloroethylidene)cyclopentane (133693-88-6) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (359436-35-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH; NaI / tetrahydrofuran

2: 95 percent / TBAF / tetrahydrofuran

3: 98 percent / NaH / tetrahydrofuran / -30 - 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00782-1

Reference yield:

[(3aS,4R,6S,6aS)-6-(tert-Butyl-dimethyl-silanyloxy)-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl]-carbamic acid benzyl ester (302906-14-5) → Dithiocarbonic acid O-{(3aR,4S,6R,6aS)-6-[benzyloxycarbonyl-(2-cyclopentylidene-ethyl)-amino]-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl} ester S-methyl ester (359436-35-4)

Guidance literature:

Multi-step reaction with 3 steps

1: 75 percent / NaH; NaI / tetrahydrofuran

2: 95 percent / TBAF / tetrahydrofuran

3: 98 percent / NaH / tetrahydrofuran / -30 - 0 °C

With tetrabutyl ammonium fluoride; sodium hydride; sodium iodide; In tetrahydrofuran;

DOI:10.1016/S0040-4039(01)00782-1

upstream raw materials:

carbon disulfide

(2-Cyclopentylidene-ethyl)-((3aS,4R,6S,6aR)-6-hydroxy-2,2-dimethyl-tetrahydro-cyclopenta[1,3]dioxol-4-yl)-carbamic acid benzyl ester

methyl iodide

(2-chloroethylidene)cyclopentane

Downstream raw materials:

(3aS,3bR,6S,6aS,7aR)-2,2-Dimethyl-6-(2-trifluoromethanesulfonyloxy-cyclopent-2-enyl)-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

(3aS,3bR,6S,6aS,7aR)-6-(2-Hydroxy-3-methoxycarbonyl-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

(3aS,3bR,6S,6aS,7aR)-6-(3-Methoxycarbonyl-2-oxo-cyclopentyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

(3aS,3bR,6R,6aS,7aR)-6-(3-Methoxycarbonyl-cyclopent-2-enyl)-2,2-dimethyl-hexahydro-1,3-dioxa-4-aza-cyclopenta[a]pentalene-4-carboxylic acid benzyl ester

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