((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

Base Information

Chemical Name:((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol
CAS No.:474799-89-8
Molecular Formula:C₃₄H₃₇NO₄
Molecular Weight:523.672
Hs Code.:

Synonyms:((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

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Chemical Property of ((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

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Technology Process of ((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

There total 12 articles about ((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol 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: 80.0%

: 1454797-31-9
(2S,3S,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)pyrrolidine

: 474799-89-8
((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 0 ℃; for 1h; Inert atmosphere;
DOI:10.1021/jo401613v

Reference yield:

: 474799-88-7
(2S,3R,4S,5S)-1-Benzyl-3,4-bis-benzyloxy-5-benzyloxymethyl-pyrrolidine-2-carbaldehyde

: 474799-89-8
((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

Guidance literature:: With sodium tetrahydroborate; In water; acetonitrile; at 0 - 20 ℃;
DOI:10.1021/jo020252d

Reference yield:

: 622-30-0
N-benzyl hydroxylalmine

: 474799-89-8
((2R,3R,4S,5S)-1-benzyl-3,4-bis(benzyloxy)-5-(benzyloxymethyl)-pyrrolidin-2-yl)methanol

Guidance literature:: Multi-step reaction with 6 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

5.1: 4 Angstroem molecular sieves; methyl triflate / acetonitrile / 0.5 h

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

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

6.1: 0.47 g / NaBH₄ / acetonitrile; H₂O / 0 - 20 °C

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