Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

Base Information

Chemical Name:Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester
CAS No.:213337-97-4
Molecular Formula:C₃₀H₃₀O₇S
Molecular Weight:534.63
Hs Code.:

Synonyms:Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

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Chemical Property of Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

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Technology Process of Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

There total 5 articles about Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl 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: 88.0%

: 108-24-7
acetic anhydride

: 213337-91-8
(3aR,4S,5R,6R,6aS)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

: 213337-97-4
Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

Guidance literature:: With trimethylsilyl trifluoromethanesulfonate; at 20 ℃; for 17h;
DOI:10.1021/jo980831b

Reference yield:

: 4291-69-4,6386-24-9,6564-72-3,59531-24-7,69257-52-9,78184-89-1,78609-16-2,78609-17-3,78609-18-4,96553-53-6,104111-61-7,131347-08-5,4132-28-9
2,3,4,6-Tetra-O-benzyl-D-glucopyranose

: 213337-97-4
Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 98 percent / NaBH₄ / ethanol; CH₂Cl₂ / 20 °C

2: (COCl)2; DMSO; Et₃N / tetrahydrofuran / 1.75 h / -65 - 20 °C

3: 3.54 g / SmI₂; t-BuOH / tetrahydrofuran / -50 - 20 °C

4: 45 percent / toluene / 4 h / 110 °C

5: 88 percent / TMSOTf / 17 h / 20 °C

With sodium tetrahydroborate; samarium diiodide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In tetrahydrofuran; ethanol; dichloromethane; toluene; 1: Reduction / 2: Swern oxidation / 3: Cyclization / 4: Cyclization / 5: acetolysis;
DOI:10.1021/jo980831b

Reference yield:

: 78136-16-0,14233-48-8
2,3,4,6-tetra-O-benzyl-D-glucitol

: 213337-97-4
Acetic acid (3aR,4S,5R,6R,6aS)-4,5,6-tris-benzyloxy-2-thioxo-tetrahydro-cyclopenta[1,3]dioxol-3a-ylmethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: (COCl)2; DMSO; Et₃N / tetrahydrofuran / 1.75 h / -65 - 20 °C

2: 3.54 g / SmI₂; t-BuOH / tetrahydrofuran / -50 - 20 °C

3: 45 percent / toluene / 4 h / 110 °C

4: 88 percent / TMSOTf / 17 h / 20 °C

With samarium diiodide; oxalyl dichloride; trimethylsilyl trifluoromethanesulfonate; dimethyl sulfoxide; triethylamine; tert-butyl alcohol; In tetrahydrofuran; toluene; 1: Swern oxidation / 2: Cyclization / 3: Cyclization / 4: acetolysis;
DOI:10.1021/jo980831b