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

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Chemical Name:(2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine
CAS No.:474799-87-6
Molecular Formula:C₃₆H₃₆N₂O₃S
Molecular Weight:576.759
Hs Code.:

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

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Chemical Property of (2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

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Technology Process of (2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

There total 5 articles about (2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)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: 66.0%

: 474799-86-5
(1S,2R,3S,4R)-1-N-benzylamino-2,3,5-tribenzyloxy-1-(1,3-thiazol-2-yl)-4-pentanol

: 474799-87-6
(2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

Guidance literature:: With pyridine; trifluoromethylsulfonic anhydride; 4 A molecular sieve; at 40 ℃; for 0.5h;
DOI:10.1021/jo020252d

Reference yield:

: 622-30-0
N-benzyl hydroxylalmine

: 474799-87-6
(2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / 0.5 h / 110 °C

2.1: n-BuLi / hexane; diethyl ether / -78 - -70 °C

2.2: 52 percent / tetrahydrofuran; diethyl ether; hexane / 5 h / -70 °C

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

4.1: 66 percent / 4 Angstroem molecular sieves; pyridine; Tf₂O / 0.5 h / 40 °C

With pyridine; n-butyllithium; trifluoromethylsulfonic anhydride; 4 A molecular sieve; copper diacetate; zinc; In diethyl ether; hexane; water; acetic acid;
DOI:10.1021/jo020252d

Reference yield:

: 16838-89-4,17073-88-0,60933-68-8,60933-69-9,73068-66-3,89361-52-4,89615-42-9,89615-45-2,96192-07-3
2,3,5-tri-O-benzyl-D-lyxofuranoside

: 474799-87-6
(2S,3R,4S,5S)-N-benzyl-3,4-dibenzyloxy-5-benzyloxymethyl-2-(1,3-thiazol-2-yl)pyrrolidine

Guidance literature:: Multi-step reaction with 4 steps

1.1: 82 percent / 0.5 h / 110 °C

2.1: n-BuLi / hexane; diethyl ether / -78 - -70 °C

2.2: 52 percent / tetrahydrofuran; diethyl ether; hexane / 5 h / -70 °C

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

4.1: 66 percent / 4 Angstroem molecular sieves; pyridine; Tf₂O / 0.5 h / 40 °C

With pyridine; n-butyllithium; trifluoromethylsulfonic anhydride; 4 A molecular sieve; copper diacetate; zinc; In diethyl ether; hexane; water; acetic acid;
DOI:10.1021/jo020252d