(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

Base Information

Chemical Name:(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester
CAS No.:911291-43-5
Molecular Formula:C₅₀H₅₀N₄O₉
Molecular Weight:850.968
Hs Code.:

(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

Synonyms:(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

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Chemical Property of (2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

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Technology Process of (2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

There total 6 articles about (2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester 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: 79.0%

: 911291-42-4
(2S,4R)-4-((2R,3S,4S,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-3-trifluoromethanesulfonyloxy-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

: 911291-43-5
(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: With sodium azide; In N,N-dimethyl-formamide; at 20 ℃; for 2h;
DOI:10.1021/ol061424m

Reference yield:

: 853245-42-8
Fmoc-cis-Hyp-O-Allyl

: 911291-43-5
(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 89 percent / pyridine / CH₂Cl₂ / 3 h / -10 - 20 °C

2.1: dibutyltin oxide / toluene / 3 h / 60 °C

2.2: 60 percent / molrcular sieves; CsF / CH₂Cl₂ / 18 h / 20 °C

3.1: 85 percent / pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

4.1: 79 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

With pyridine; sodium azide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol061424m

Reference yield:

: 911291-38-8
(2S,4S)-4-Trifluoromethanesulfonyloxy-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

: 911291-43-5
(2S,4R)-4-((2R,3R,4R,5S,6R)-3-Azido-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-pyrrolidine-1,2-dicarboxylic acid 2-allyl ester 1-(9H-fluoren-9-ylmethyl) ester

Guidance literature:: Multi-step reaction with 3 steps

1.1: dibutyltin oxide / toluene / 3 h / 60 °C

1.2: 60 percent / molrcular sieves; CsF / CH₂Cl₂ / 18 h / 20 °C

2.1: 85 percent / pyridine / CH₂Cl₂ / 2 h / 0 - 20 °C

3.1: 79 percent / NaN₃ / dimethylformamide / 2 h / 20 °C

With pyridine; sodium azide; di(n-butyl)tin oxide; In dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1021/ol061424m