(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

Base Information

Chemical Name:(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine
CAS No.:113299-94-8
Molecular Formula:C₂₉H₃₃NO₃
Molecular Weight:443.586
Hs Code.:

Synonyms:(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

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Technology Process of (2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

There total 14 articles about (2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine 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: 56.0%

: 154815-50-6
(2S,3R,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidine-2-carbaldehyde

: 762-72-1
allyl-trimethyl-silane

: 113299-94-8
(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

Guidance literature:: With titanium tetrachloride; In dichloromethane; at -78 ℃; for 1h;
DOI:10.1248/cpb.41.1717

Reference yield: 48.0%

: 154815-50-6
(2S,3R,4R)-1-Benzyl-3,4-bis-benzyloxy-pyrrolidine-2-carbaldehyde

: 113200-92-3
(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1R)-1-hydroxy-3-butenyl>-pyrrolidine

: 113299-94-8
(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

Guidance literature:: In diethyl ether; at -78 ℃; for 0.5h;
DOI:10.1248/cpb.41.1717

Reference yield:

: 100-39-0
benzyl bromide

: 113299-94-8
(2R,3R,4R)-N-benzyl-3,4-bis(benzyloxy)-2-<(1S)-1-hydroxy-3-butenyl>-pyrrolidine

Guidance literature:: Multi-step reaction with 9 steps

1: 1.) NaH / 1.)THF, DMF, RT, 1 h, 2.) THF, DMF, RT, 15 h

2: 1.) LDA / 1.) THF, hexane, -78 deg C, 40 min, 2.) THF, hexane, -78 deg C, 15 min

3: 84 percent / 30percent H₂O₂ / ethyl acetate / 0.33 h / 15 - 20 °C

4: 6 percent / OsO₄, N-methylmorpholine N-oxide / acetone; H₂O / 13 h / Ambient temperature

5: 1.) NaH / 1.) THF, DMF, RT, 30 min, 2.) HF, DMF, RT, 3 h

6: 65 percent / NaOMe / methanol; tetrahydrofuran / 5 h / Ambient temperature

7: 82 percent / a) borane-dimethyl sulfide complex, b) 10percent aq. HCl / a) THF, 70 deg C, 1 h, b) THF, MeOH, 70 deg C, 1 h

8: DMSO, oxalyl chloride / CH₂Cl₂ / a) -20 deg C,

9: 30 percent / tetrahydrofuran / 1 h / -78 °C

With hydrogenchloride; osmium(VIII) oxide; oxalyl dichloride; dimethylsulfide borane complex; dihydrogen peroxide; sodium methylate; sodium hydride; dimethyl sulfoxide; 4-methylmorpholine N-oxide; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; acetone;
DOI:10.1248/cpb.41.1717