(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Base Information

Chemical Name:(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester
CAS No.:905578-53-2
Molecular Formula:C₂₄H₃₁NO₁₀
Molecular Weight:493.511
Hs Code.:

(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Synonyms:(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

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Chemical Property of (3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

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Technology Process of (3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

There total 14 articles about (3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl 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: 85.0%

: (3aS,5aR,7S,8aS,8bS)-7-((Z)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-vinyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

: 905578-53-2
(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Guidance literature:: With hydrogen; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In tetrahydrofuran; at 20 ℃; for 96h; under 6000.48 Torr;
DOI:10.1021/jo0605593

Reference yield:

: 905578-50-9
((3aS,5aR,8aS,8bS)-7-Benzyloxymethyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-ylmethoxy)-tert-butyl-dimethyl-silane

: 905578-53-2
(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 75 percent / hydrogen / Pd/C / hexane / 2 h / 20 °C

2: SO₃*pyridine; DMSO; triethylamine / CH₂Cl₂ / 1.5 h / 20 °C

3: NaClO₂; 2-methyl-2-butene; NaH₂PO₄ / 2-methyl-propan-2-ol; H₂O / 2 h / 20 °C

4: 10.6 g / methanol; benzene; diethyl ether / 20 °C

5: 85 percent / TBAF / tetrahydrofuran / 0.5 h / 20 °C

6: oxalyl chloride; DMSO; triethylamine / CH₂Cl₂ / 1.75 h / -78 - 20 °C

7: 5.65 g / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 1 h / 20 °C

8: 85 percent / hydrogen / [Rh(COD){(S,S)-EtDuPHOS}]OTf / tetrahydrofuran / 96 h / 20 °C / 6000.48 Torr

With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; oxalyl dichloride; pyridine-SO₃ complex; tetrabutyl ammonium fluoride; hydrogen; dimethyl sulfoxide; triethylamine; N,N,N',N'-tetramethylguanidine; palladium on activated charcoal; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; tert-butyl alcohol; benzene; 6: Swern oxidation / 7: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo0605593

Reference yield:

: (3aS,5aR,7S,8aS,8bS)-7-Formyl-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

: 905578-53-2
(3aS,5aR,7R,8aS,8bS)-7-((S)-2-Benzyloxycarbonylamino-2-methoxycarbonyl-ethyl)-2,2-dimethyl-hexahydro-[1,3]dioxolo[4,5]furo[2,3-b]pyran-7-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 5.65 g / N,N,N',N'-tetramethylguanidine / CH₂Cl₂ / 1 h / 20 °C

2: 85 percent / hydrogen / [Rh(COD){(S,S)-EtDuPHOS}]OTf / tetrahydrofuran / 96 h / 20 °C / 6000.48 Torr

With hydrogen; N,N,N',N'-tetramethylguanidine; [(1,2,5,6-r)-1,5-cyclooctadiene][(2S,2'S,5 S,5'S)-1,1'-(1,2-phenylene)bis[2,5-diethylphospholane-κP]]-rhodium(1+) trifluoromethanesulfonate; In tetrahydrofuran; dichloromethane; 1: Horner-Wadsworth-Emmons olefination;
DOI:10.1021/jo0605593