(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

Base Information

Chemical Name:(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde
CAS No.:298700-87-5
Molecular Formula:C₃₄H₃₅NO₄
Molecular Weight:521.656
Hs Code.:

Synonyms:(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

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Chemical Property of (2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

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Technology Process of (2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

There total 7 articles about (2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde 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:

: 260789-58-0
(2S,3R,4R,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

: 298700-87-5
(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

Guidance literature:: (2S,3R,4R,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine; With methyl trifluoromethanesulfonate; In acetonitrile; at 20 ℃;

With sodium tetrahydroborate; In methanol; at 20 ℃;

With mercury dichloride; In water; acetonitrile; at 20 ℃;
DOI:10.1016/S0040-4039(99)01987-5

Reference yield:

: 260789-54-6
(1SR,2R,3R,4R)-1-N-benzylhydroxylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

: 298700-87-5
(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 3 steps

1.1: 78 percent / (AcO)2Cu*H₂O; Zn / acetic acid; H₂O / 0.75 h / 20 - 70 °C

2.1: 65 percent / 4 Angstroem molecular sieves; pyridine; Tf₂O / 0.5 h / 40 °C

3.1: 4 Angstroem molecular sieves; methyl triflate / acetonitrile / 0.5 h

3.2: NaBH₄ / methanol / 0.17 h / 20 °C

3.3: AgNO₃ / acetonitrile; H₂O / 0.17 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; copper diacetate; methyl trifluoromethanesulfonate; zinc; In water; acetic acid; acetonitrile;
DOI:10.1021/jo020252d

Reference yield:

: 260789-56-8
(1S,2R,3R,4R)-1-N-benzylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

: 298700-87-5
(2S,3R,4R,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

Guidance literature:: Multi-step reaction with 2 steps

1.1: 65 percent / 4 Angstroem molecular sieves; pyridine; Tf₂O / 0.5 h / 40 °C

2.1: 4 Angstroem molecular sieves; methyl triflate / acetonitrile / 0.5 h

2.2: NaBH₄ / methanol / 0.17 h / 20 °C

2.3: AgNO₃ / acetonitrile; H₂O / 0.17 h / 20 °C

With pyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; methyl trifluoromethanesulfonate; In acetonitrile;
DOI:10.1021/jo020252d