(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

Base Information

Chemical Name:(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one
CAS No.:313218-78-9
Molecular Formula:C₂₄H₂₈O₈S
Molecular Weight:476.548
Hs Code.:

Synonyms:(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

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Chemical Property of (3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

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Technology Process of (3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

There total 12 articles about (3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-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:

: 313218-77-8
(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-ol

: 313218-78-9
(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

Guidance literature:: In acetone; at 0 ℃; Yield given; Jones oxidn.;
DOI:10.1016/S0040-4039(97)10660-8

Reference yield:

: 203248-24-2
(R)-4-(tert-butyldimethylsilyl)oxy-2-(methoxymethyl)oxybutan-1-ol

: 313218-78-9
(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

2.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C

3.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

4.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

5.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

6.1: TBAF / tetrahydrofuran / 1 h / 20 °C

7.1: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

8.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: 99 percent / tetrahydrofuran / -78 - 20 °C

9.1: OsO₄; NaIO₄ / dioxane; H₂O / 24 h

10.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; jones reagent; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Oxidation / 2.1: Horner-Emmons reaction / 3.1: Reduction / 4.1: Epoxidation / 5.1: Alkylation / 6.1: desilylation / 7.1: mesylation / 8.1: Metallation / 8.2: Cyclization / 9.1: Oxidation / 10.1: Oxidation;
DOI:10.1016/S0040-4020(00)00730-4

Reference yield:

: 313218-73-4
(R)-3-Methoxymethoxy-4-trityloxy-butan-1-ol

: 313218-78-9
(3S,3aS,4R,6aR)-6a-Benzenesulfonyl-3-(4-methoxy-benzyloxymethyl)-4-methoxymethoxy-hexahydro-cyclopenta[c]furan-1-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole / dimethylformamide / 3 h / 20 °C

2.1: 75.0 g / liquid NH₃ / tetrahydrofuran; ethanol / 0.5 h / -34 °C

3.1: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4.1: tBuOK / tetrahydrofuran / 0.5 h / -42 °C

5.1: 12.7 g / DIBAL-H / toluene; hexane / 0.5 h / -78 °C

6.1: 89 percent / Ti(OPr-i)4; D-(-)-diethyl tartrate; TBHP / CH₂Cl₂ / 5 h / -20 °C

7.1: 95 percent / NaH / tetrahydrofuran; dimethylformamide / 1 h / 0 °C

8.1: TBAF / tetrahydrofuran / 1 h / 20 °C

9.1: 3.89 g / DMAP / CH₂Cl₂ / 0.25 h / 0 °C

10.1: BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

10.2: 99 percent / tetrahydrofuran / -78 - 20 °C

11.1: OsO₄; NaIO₄ / dioxane; H₂O / 24 h

12.1: 2.40 g / Jones reagent / acetone / 0.17 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium periodate; osmium(VIII) oxide; n-butyllithium; jones reagent; oxalyl dichloride; diethyl (2S,3S)-tartrate; potassium tert-butylate; tetrabutyl ammonium fluoride; ammonia; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; 1,4-dioxane; ethanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; 1.1: Substitution / 2.1: detritylation / 3.1: Oxidation / 4.1: Horner-Emmons reaction / 5.1: Reduction / 6.1: Epoxidation / 7.1: Alkylation / 8.1: desilylation / 9.1: mesylation / 10.1: Metallation / 10.2: Cyclization / 11.1: Oxidation / 12.1: Oxidation;
DOI:10.1016/S0040-4020(00)00730-4