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

Base Information

Chemical Name:(2S,3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-pyrrolidine
CAS No.:1454797-16-0
Molecular Formula:C₅₃H₅₁NO₄
Molecular Weight:765.992
Hs Code.:

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

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

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

There total 5 articles about (2S,3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-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: 76.0%

: 1454797-14-8
(2R,3S,4S,5R)-1,3,4-tris(benzyloxy)-6-(trityloxy)hexane-2,5-diyl dimethanesulfonate

: 100-46-9
benzylamine

: 1454797-16-0
(2S,3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-pyrrolidine

Guidance literature:: at 140 ℃; for 6h; Inert atmosphere;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-05-7
(2R,3S,4R)-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-3,4-dihydro-2H-pyran

: 1454797-16-0
(2S,3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 5 steps

1: 4-methylmorpholine N-oxide; osmium(VIII) oxide / acetone; tert-butyl alcohol; water / 20 °C / Inert atmosphere

2: sodium periodate / water; acetonitrile / 5 h / 20 °C / Inert atmosphere

3: sodium tetrahydroborate / methanol / 1.25 h / 0 °C / Inert atmosphere

4: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

5: 6 h / 140 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; 4-methylmorpholine N-oxide; triethylamine; In methanol; dichloromethane; water; acetone; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo401613v

Reference yield:

: 1454797-09-1
(2R,3R,4S)-1,3,4-tris(benzyloxy)-5-oxo-6-(trityloxy)hexan-2-yl formate

: 1454797-16-0
(2S,3R,4R,5R)-1-benzyl-3,4-bis(benzyloxy)-2-(benzyloxymethyl)-5-(trityloxymethyl)-pyrrolidine

Guidance literature:: Multi-step reaction with 3 steps

1: sodium tetrahydroborate / methanol / 1.25 h / 0 °C / Inert atmosphere

2: triethylamine; dmap / dichloromethane / 1 h / 0 °C / Inert atmosphere

3: 6 h / 140 °C / Inert atmosphere

With dmap; sodium tetrahydroborate; triethylamine; In methanol; dichloromethane;
DOI:10.1021/jo401613v