(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Base Information

Chemical Name:(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester
CAS No.:300676-91-9
Molecular Formula:C₂₃H₂₇NO₅
Molecular Weight:397.471
Hs Code.:

Synonyms:(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

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Chemical Property of (2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

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Technology Process of (2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

There total 9 articles about (2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl 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: 93.0%

: 300676-90-8
3-hydroxy-6-methoxy-4a-methyl-1-vinyl-3,4,4a,9a-tetrahydro-1H-pyrano[3,4-b]indole-9-carboxylic acid benzyl ester

: 300676-91-9
(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Guidance literature:: With sodium tetrahydroborate; In ethanol;
DOI:10.1021/ol006065o

Reference yield:

: 221015-46-9
(1S,5S,7R)-7-(tert-Butyl-dimethyl-silanyloxymethyl)-6,8-dioxa-bicyclo[3.2.1]oct-3-en-2-one

: 300676-91-9
(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 92 percent / H₂ / Pd-C / ethyl acetate

2: 70 percent / LHMDS; HMPA / tetrahydrofuran

3: 70 percent / pyridine; H₂O / 2.5 h / Heating

4: LiAlH₄ / tetrahydrofuran / 0 °C

5: aq. K₂CO₃

6: 89 percent / TBAF / tetrahydrofuran

7: 97 percent / Zn; AcOH / ethanol / Heating

8: 93 percent / NaBH₄ / ethanol

With N,N,N,N,N,N-hexamethylphosphoric triamide; sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; hydrogen; potassium carbonate; acetic acid; lithium hexamethyldisilazane; zinc; palladium on activated charcoal; In tetrahydrofuran; pyridine; ethanol; water; ethyl acetate; 1: Hydrogenation / 2: Methylation / 3: <3,3>-sigmatropic rearrangement; cyclization / 4: Reduction / 5: Condensation / 6: Hydrolysis / 7: reductive cleavage / 8: Reduction;
DOI:10.1021/ol006065o

Reference yield:

: 19501-58-7
4-methoxyphenylhydrazine hydrochloride

: 300676-91-9
(2R,3S)-2-((S)-1-Hydroxy-allyl)-3-(2-hydroxy-ethyl)-5-methoxy-3-methyl-2,3-dihydro-indole-1-carboxylic acid benzyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 70 percent / pyridine; H₂O / 2.5 h / Heating

2: LiAlH₄ / tetrahydrofuran / 0 °C

3: aq. K₂CO₃

4: 89 percent / TBAF / tetrahydrofuran

5: 97 percent / Zn; AcOH / ethanol / Heating

6: 93 percent / NaBH₄ / ethanol

With sodium tetrahydroborate; lithium aluminium tetrahydride; tetrabutyl ammonium fluoride; potassium carbonate; acetic acid; zinc; In tetrahydrofuran; pyridine; ethanol; water; 1: <3,3>-sigmatropic rearrangement; cyclization / 2: Reduction / 3: Condensation / 4: Hydrolysis / 5: reductive cleavage / 6: Reduction;
DOI:10.1021/ol006065o