(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

Base Information

Chemical Name:(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione
CAS No.:1352405-95-8
Molecular Formula:C₃₂H₅₅NO₇Si₂
Molecular Weight:621.962
Hs Code.:

(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

Synonyms:(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

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Chemical Property of (3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

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Technology Process of (3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

There total 11 articles about (3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione 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: 90.0%

: 1352405-91-4
(3R,3aS,4S,6aS)-4-[(2R,3R)-4-(benzyloxy)-3-hydroxy-2-methylbutyl]-3a-hydroxy-6a-(hydroxymethyl)-3-methyldihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 1352405-95-8
(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

Guidance literature:: With 2,6-dimethylpyridine; In N,N-dimethyl-formamide; at -10 ℃; for 2h;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-61-8
(3S,7aR)-methyl 7-((3R,4R,1E)-5-(benzyloxy)-4-hydroxy-3-methylpent-1-enyl)-3-tert-butyl-6-methyl-5-oxo-1,3,5,7a-tetrahydropyrrolo[1,2-c]oxazole-7a-carboxylate

: 1352405-95-8
(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

Guidance literature:: Multi-step reaction with 7 steps

1.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

2.1: 2,6-dimethylpyridine / dichloromethane / 0.67 h / -10 °C

3.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C

4.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol / 144 h / 20 °C / Darkness

4.2: 12 h / 20 °C

5.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / chloroform / 24 h / 20 °C

6.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol / 0.75 h / 20 °C

7.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / -10 °C

With 2,6-dimethylpyridine; 1.3-propanedithiol; hydrogenchloride; osmium(VIII) oxide; water; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;
DOI:10.1016/j.tet.2011.09.037

Reference yield:

: 1352405-63-0
(2R,3R)-1-(menzyloxy)-3-methyl-5-(tri-n-butylstannyl)-4-penten-2-ol

: 1352405-95-8
(3R,3aS,4S,6aS)-4-{(2R,3R)-4-(benzyloxy)-2-methyl-3-[triethylsilyloxy]butyl}-3a-hydroxy-3-methyl-6a{triethylsilyloxymethyl}dihydro-1H-furo[3,4-b]pyrrole-2,6(3H,4H)-dione

Guidance literature:: Multi-step reaction with 8 steps

1.1: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; trifuran-2-yl-phosphane / N,N-dimethyl-formamide / 0.08 h / 20 °C

1.2: 15 h / 50 °C

2.1: sodium acetate; toluene-4-sulfonic acid hydrazide / 1,2-dimethoxyethane; water / Reflux

3.1: 2,6-dimethylpyridine / dichloromethane / 0.67 h / -10 °C

4.1: potassium hexamethylsilazane / tetrahydrofuran; toluene / 0.75 h / -78 °C

5.1: osmium(VIII) oxide; water; 4-methylmorpholine N-oxide / tert-butyl alcohol / 144 h / 20 °C / Darkness

5.2: 12 h / 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / chloroform / 24 h / 20 °C

7.1: 1.3-propanedithiol; hydrogenchloride / 2,2,2-trifluoroethanol / 0.75 h / 20 °C

8.1: 2,6-dimethylpyridine / N,N-dimethyl-formamide / 2 h / -10 °C

With 2,6-dimethylpyridine; 1.3-propanedithiol; hydrogenchloride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; osmium(VIII) oxide; trifuran-2-yl-phosphane; water; sodium acetate; potassium hexamethylsilazane; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; toluene-4-sulfonic acid hydrazide; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; chloroform; 2,2,2-trifluoroethanol; water; N,N-dimethyl-formamide; toluene; tert-butyl alcohol; 1.1: Stille coupling;
DOI:10.1016/j.tet.2011.09.037