methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

Base Information

Chemical Name:methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate
CAS No.:1197398-05-2
Molecular Formula:C₂₄H₂₃FO₆
Molecular Weight:426.441
Hs Code.:

Synonyms:methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

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Chemical Property of methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

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Technology Process of methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

There total 16 articles about methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-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:

: 1197398-04-1
methyl (1R,2R,5S,6S)-2-(acetyloxy)-6-fluoro-4-oxobicyclo[3.1.0]hexane-6-carboxylate

: 852395-27-8
(4S,5S)-2,2,7,7-tetramethyl-4,5-diphenyl-3,6-dioxa-2,7-disilaoctane

: 1197398-05-2
methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

Guidance literature:: methyl (1R,2R,5S,6S)-2-(acetyloxy)-6-fluoro-4-oxobicyclo[3.1.0]hexane-6-carboxylate; (4S,5S)-2,2,7,7-tetramethyl-4,5-diphenyl-3,6-dioxa-2,7-disilaoctane; With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -10 ℃;

With pyridine; In dichloromethane; at 0 ℃; for 0.333333h;

Reference yield:

: 1197398-04-1
methyl (1R,2R,5S,6S)-2-(acetyloxy)-6-fluoro-4-oxobicyclo[3.1.0]hexane-6-carboxylate

: 2325-10-2
(S,S)-hydrobenzoin

: 1197398-05-2
methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

Guidance literature:: With trifluorormethanesulfonic acid; In dichloromethane; at -5 - 20 ℃; for 22h;

Reference yield:

: 77-73-6,933-60-8,1755-01-7,25038-78-2
bi(cyclopentadiene)

: 1197398-05-2
methyl (1S,4R,4'S,5R,5'S,6S)-4-(acetyloxy)-6-fluoro-4',5'-diphenylspiro[bicyclo[3.1.0]hexane-2,2-[1,3]dioxolane]-6-carboxylate

Guidance literature:: Multi-step reaction with 9 steps

1.1: 185 - 190 °C

2.1: peracetic acid; sodium carbonate / dichloromethane / 23 h / -15 - 20 °C

3.1: sodium methylate / methanol / 0.25 h / 25 - 30 °C

3.2: 1.03 h / 20 - 38 °C

4.1: lithium chloride / water; dimethyl sulfoxide / 2 h / 130 °C

5.1: tert.-butylhydroperoxide / bis(acetylacetonate)oxovanadium / toluene; chlorobenzene / 4.17 h / 20 - 60 °C

6.1: triethylaluminum / hexane; tetrahydrofuran / 0.5 h / -60 - -50 °C

6.2: 2.75 h / -50 - -40 °C

6.3: 0.5 h / 5 °C

7.1: Candida antarctica-derived lipase A (NOVOZYM 735) immobilized on Toyonite 200M / acetone / Enzymatic reaction

8.1: sodium hydrogencarbonate; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical / dichloromethane; water / 1 h / -10 - 0 °C

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / -10 °C

9.2: 0.33 h / 0 °C

With tert.-butylhydroperoxide; peracetic acid; sodium hypochlorite; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; trimethylsilyl trifluoromethanesulfonate; triethylaluminum; sodium methylate; sodium hydrogencarbonate; sodium carbonate; lithium chloride; bis(acetylacetonate)oxovanadium; In tetrahydrofuran; methanol; hexane; dichloromethane; water; dimethyl sulfoxide; chlorobenzene; acetone; toluene;