(1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

Base Information

Chemical Name:(1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol
CAS No.:1555994-24-5
Molecular Formula:C₁₂H₂₁NO₃
Molecular Weight:227.304
Hs Code.:

Synonyms:(1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

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Chemical Property of (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

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Technology Process of (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

There total 2 articles about (1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol 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

: 1555994-24-5
(1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

Guidance literature:: Multi-step reaction with 7 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

7: palladium on activated charcoal; hydrogen / methanol / 20 °C / 2585.81 Torr

With sodium tetrahydroborate; thionyl chloride; acid phosphatase; palladium on activated charcoal; fuculose-1-phosphate aldolase variant F₁₃₁A; hydrogen; 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

: 1555994-24-5
(1S,2S,3R,4aS,8aS,9aS)-3-(hydroxymethyl)decahydro-1H-pyrrolo[1,2-a]indole-1,2-diol

Guidance literature:: Multi-step reaction with 7 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

7: palladium on activated charcoal; hydrogen / methanol / 20 °C / 2585.81 Torr

With sodium tetrahydroborate; thionyl chloride; acid phosphatase; palladium on activated charcoal; fuculose-1-phosphate aldolase variant F₁₃₁A; hydrogen; 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