(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

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Chemical Name:(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate
CAS No.:955959-40-7
Molecular Formula:C₂₁H₂₇NO₇
Molecular Weight:405.448
Hs Code.:

Synonyms:(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

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Chemical Property of (3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

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Technology Process of (3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

There total 5 articles about (3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate 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: 100.0%

: 955959-41-8
(R,E)-dimethyl 3-((R)-4-(benzyloxy)-3-methylbutylidene)-1,4-dimethyl-5-oxopyrrolidine-2,2-dicarboxylate

: 955959-40-7
(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

Guidance literature:: With osmium(VIII) oxide; 4-methylmorpholine N-oxide; In tetrahydrofuran; water; at 20 ℃; for 41h; Inert atmosphere;
DOI:10.1021/ol202306d

Reference yield:

: 955959-44-1
((2R,6R)-7-benzyloxy)-2,6-dimethylhept-3-yn-1-ol

: 955959-40-7
(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1: Jones reagent / acetone / 4 h / 0 °C / Inert atmosphere

2: thionyl chloride / toluene / 10 h / 0 - 20 °C / Inert atmosphere

3: toluene / 2 h / 0 - 20 °C / Inert atmosphere

4: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Inert atmosphere; Reflux

5: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 41 h / 20 °C / Inert atmosphere

With indium(III) triflate; osmium(VIII) oxide; Jones reagent; thionyl chloride; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; water; acetone; toluene; 1: Jones oxidation;
DOI:10.1021/ol202306d

Reference yield:

: 1332721-77-3
dimethyl 2-((2R,6R)-7-(benzyloxy)-N,2,6-trimethylhept-3-ynamido)malonate

: 955959-40-7
(3R,3aS,4S,6aR)-methyl 4-((R)-3-(benzyloxy)-2-methylpropyl)-hexahydro-3a-hydroxy-1,3-dimethyl-2,6-dioxo-1H-furo[3,4-b]pyrrole-6a-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1: indium(III) triflate; 1,8-diazabicyclo[5.4.0]undec-7-ene / toluene / 6 h / Inert atmosphere; Reflux

2: osmium(VIII) oxide; 4-methylmorpholine N-oxide / tetrahydrofuran; water / 41 h / 20 °C / Inert atmosphere

With indium(III) triflate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In tetrahydrofuran; water; toluene;
DOI:10.1021/ol202306d