(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Base Information

Chemical Name:(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate
CAS No.:391612-42-3
Molecular Formula:C₁₈H₁₇NO₄
Molecular Weight:311.337
Hs Code.:

Synonyms:(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

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Chemical Property of (3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

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Technology Process of (3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

There total 6 articles about (3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-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: 98.0%

: 501-53-1,94274-21-2
benzyl chloroformate

: 261785-62-0,273919-52-1
(3aR,8aS)-3,3a,8,8a-tetrahydro-2H-furo[2,3-b]indol-3a-ol

: 391612-42-3
(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Guidance literature:: With pyridine; In dichloromethane; at 0 ℃;
DOI:10.1016/j.tetlet.2005.01.016

Reference yield: 90.0%

: 1580471-24-4
(3aR,8aS)-benzyl 3a-bromo-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

: 391612-42-3
(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Guidance literature:: With water; silver trifluoroacetate; at 20 ℃; for 1h; Ionic liquid;
DOI:10.1021/ol5004109

Reference yield:

: 1580470-83-2
benzyl 3-(2-((tert-butyldimethylsilyl)oxy)ethyl)-1H-indole-1-carboxylate

: 391612-42-3
(3aR,8aS)-benzyl 3a-hydroxy-3,3a-dihydro-2H-furo[2,3-b]indole-8(8aH)-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0 - 20 °C / Inert atmosphere

2: (R)-1,1'-binaphthyl-2,2'-phosphoric acid; C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-); 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾; sodium carbonate / toluene / 2 h / 0 °C / Inert atmosphere; Enzymatic reaction

3: silver trifluoroacetate; water / 1 h / 20 °C / Ionic liquid

With C₁₅H₁₇F₆N₂⁽¹⁺⁾*Br₂*BF₄^(1-); 2C₁₅H₁₇F₆N₂⁽¹⁺⁾*3BF₄^(1-)*Br⁽¹⁺⁾; tetrabutyl ammonium fluoride; water; (R)-1,1'-binaphthyl-2,2'-phosphoric acid; silver trifluoroacetate; sodium carbonate; In tetrahydrofuran; toluene;
DOI:10.1021/ol5004109