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

Base Information

Chemical Name:(3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione
CAS No.:213337-93-0
Molecular Formula:C₃₅H₃₄O₆S
Molecular Weight:582.717
Hs Code.:

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

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Chemical Property of (3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

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Technology Process of (3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

There total 4 articles about (3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione 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: 45.0%

: 6160-65-2
1,1'-Thiocarbonyldiimidazole

: 3,4,5-tris(benzyloxy)-1-(benzyloxymethyl)-cis-1,2-cyclopentanediol

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

: 213337-93-0
(3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

Guidance literature:: In toluene; at 110 ℃; for 4h;
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

: 213337-93-0
(3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

Guidance literature:: Multi-step reaction with 4 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: 52 percent / toluene / 4 h / 110 °C

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

Reference yield:

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

: 213337-93-0
(3aS,4S,5R,6R,6aR)-4,5,6-Tris-benzyloxy-3a-benzyloxymethyl-tetrahydro-cyclopenta[1,3]dioxole-2-thione

Guidance literature:: Multi-step reaction with 3 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: 52 percent / toluene / 4 h / 110 °C

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