(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

Base Information

Chemical Name:(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one
CAS No.:878496-37-8
Molecular Formula:C₂₁H₂₃NO₅
Molecular Weight:369.417
Hs Code.:

Synonyms:(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

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Chemical Property of (1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

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Technology Process of (1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

There total 11 articles about (1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one 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: 26.0%

: 878496-32-3
(1S,2S,7aS)-1,2-bis(benzyloxy)-2,3,5,7a-tetrahydro-1H-pyrrolizine

: 878496-33-4
(1S,2R,6S,7S,7aS)-6,7-bis(benzyloxy)hexahydro-1H-pyrrolizine-1,2-diol

: 878496-35-6
(1R,2S,6S,7S,7aS)-6,7-bis(benzyloxy)hexahydro-1H-pyrrolizine-1,2-diol

: 878496-37-8
(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

Guidance literature:: With 4-methylmorpholine N-oxide; osmium(VIII) oxide; In acetone; tert-butyl alcohol; at 0 ℃; for 1h;
DOI:10.1021/jo051792o

Reference yield:

: (3R,4S,5S)-6-Allylamino-4,5-bis-benzyloxy-hex-1-en-3-ol

: 878496-37-8
(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

Guidance literature:: Multi-step reaction with 5 steps

1: 1.09 g / dioxane / 0.5 h

2: 99 percent / Grubbs 2nd generation catalyst / CH₂Cl₂ / 0.67 h / Heating

3: trifluoroacetic acid / CH₂Cl₂

4: 0.0092 g / PPh₃; diethyl azodicarboxylate / CH₂Cl₂

5: 12.9 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; 2-methyl-propan-2-ol / 1 h / 0 °C

With 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; In 1,4-dioxane; dichloromethane; acetone; tert-butyl alcohol; 4: Mitsunobu cyclization;
DOI:10.1021/jo051792o

Reference yield:

: tert-butyl (3S,4S,5R,6Z)-3,4-bis(benzyloxy)-5-hydroxy-3,4,5,8-tetrahydroazocine-1(2H)-carboxylate

: 878496-37-8
(1S,2R,6S,7R,7aS)-1,2-bis(benzyloxy)-6,7-dihydroxyhexahydro-3H-pyrrolizin-3-one

Guidance literature:: Multi-step reaction with 3 steps

1: trifluoroacetic acid / CH₂Cl₂

2: 0.0092 g / PPh₃; diethyl azodicarboxylate / CH₂Cl₂

3: 12.9 percent / N-methylmorpholine N-oxide / OsO₄ / acetone; 2-methyl-propan-2-ol / 1 h / 0 °C

With 4-methylmorpholine N-oxide; triphenylphosphine; trifluoroacetic acid; diethylazodicarboxylate; osmium(VIII) oxide; In dichloromethane; acetone; tert-butyl alcohol; 2: Mitsunobu cyclization;
DOI:10.1021/jo051792o