(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

Base Information

Chemical Name:(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole
CAS No.:1555994-26-7
Molecular Formula:C₂₀H₂₇NO₆
Molecular Weight:377.437
Hs Code.:

Synonyms:(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

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Chemical Property of (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

Chemical Property:

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Technology Process of (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

There total 10 articles about (2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole 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:

: 80828-13-3,80875-98-5,82717-40-6,87679-20-7,87679-39-8,87679-51-4,87679-58-1,88547-85-7,88585-94-8,96844-78-9,108507-42-2,145438-94-4,145438-95-5,145513-90-2,145513-91-3,145513-92-4,145513-93-5,2055118-14-2
(+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid

: 1555994-26-7
(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-29-0
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-31-4
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

Guidance literature:: Multi-step reaction with 6 steps

1: thionyl chloride / 24 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

3: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; methanol / 2 h / 20 °C

4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

5: fuculose-1-phosphate aldolase variant F₁₃₁A / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / pH 7.5 / Enzymatic reaction

6: acid phosphatase / aq. buffer / 12 h / pH 4.5 / Enzymatic reaction

With sodium tetrahydroborate; thionyl chloride; acid phosphatase; fuculose-1-phosphate aldolase variant F₁₃₁A; N-ethyl-N,N-diisopropylamine; calcium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5: |Aldol Addition;
DOI:10.1021/ol5002158

Reference yield:

: 80828-13-3,80875-98-5,82717-40-6,87679-20-7,87679-39-8,87679-51-4,87679-58-1,88547-85-7,88585-94-8,96844-78-9,108507-42-2,145438-94-4,145438-95-5,145513-90-2,145513-91-3,145513-92-4,145513-93-5,2055118-14-2
(+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid

: 1555994-26-7
(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-29-0
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-31-4
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

Guidance literature:: Multi-step reaction with 6 steps

1: thionyl chloride / 24 h / 20 °C / Cooling with ice

2: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

3: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; methanol / 2 h / 20 °C

4: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

5: fuculose-1-phosphate aldolase variant F₁₃₁A / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / pH 7.5 / Enzymatic reaction

6: acid phosphatase / aq. buffer / 12 h / pH 4.5 / Enzymatic reaction

With sodium tetrahydroborate; thionyl chloride; acid phosphatase; fuculose-1-phosphate aldolase variant F₁₃₁A; N-ethyl-N,N-diisopropylamine; calcium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 5: |Aldol Addition;
DOI:10.1021/ol5002158

Reference yield:

: C₁₀H₁₇NO₂

: 1555994-26-7
(2S,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-29-0
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

: 1555994-31-4
(2R,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole

Guidance literature:: Multi-step reaction with 5 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 20 °C

2: sodium tetrahydroborate; calcium chloride / tetrahydrofuran; methanol / 2 h / 20 °C

3: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 6 h / Reflux

4: fuculose-1-phosphate aldolase variant F₁₃₁A / N,N-dimethyl-formamide / 24 h / 0 - 4 °C / pH 7.5 / Enzymatic reaction

5: acid phosphatase / aq. buffer / 12 h / pH 4.5 / Enzymatic reaction

With sodium tetrahydroborate; acid phosphatase; fuculose-1-phosphate aldolase variant F₁₃₁A; N-ethyl-N,N-diisopropylamine; calcium chloride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; 4: |Aldol Addition;
DOI:10.1021/ol5002158