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

Base Information

• Chemical Name: (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole
• CAS No.: 1555994-20-1
• Molecular Formula: C₂₀H₂₇NO₆
• Molecular Weight: 377.437
• Mol file: 1555994-20-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 11 articles about (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,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:

(+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid (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)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-20-1) + (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-22-3)

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:

(+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid (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)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-20-1) + (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-22-3)

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:

methyl N-(benzyloxycarbonyl)octahydroindole-2-carboxylate → (2S,3aS,7aS)-N-(benzyloxycarbonyl)-2-[(1'S,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-20-1) + (2R,3aR,7aR)-N-(benzyloxycarbonyl)-2-[(1'R,2'R)-1,2,4-trihydroxy-3-oxobutyl]octahydroindole (1555994-22-3)

Guidance literature:

Multi-step reaction with 4 steps

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

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

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

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

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

DOI:10.1021/ol5002158

upstream raw materials:

(+/-)-(2S,3aS,7aS)-octahydroindole-2-carboxylic acid

(+/-)-(2R,3aS,7aS)-octahydroindole-2-carboxylic acid

C₂₀H₂₈NO₉P