(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

Base Information

Chemical Name:(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine
CAS No.:909192-26-3
Molecular Formula:C₂₂H₂₇NO₅
Molecular Weight:385.46
Hs Code.:

Synonyms:

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Chemical Property of (1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

Chemical Property:

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Technology Process of (1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

There total 9 articles about (1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine 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: 73.0%

: 909192-25-2
(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-3-tert-butyldiphenylsilyloxymethyl-6,7-dihydroxypyrrolizidine

: 909192-26-3
(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; for 12h; Heating;
DOI:10.1080/07328300600735181

Reference yield:

: (3R,4R,5R)-3,4-dibenzyloxy-2'-O-tert-butyldiphenylsilyl-2,5-bis(hydroxymethyl)pyrrolidine

: 909192-26-3
(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

Guidance literature:: Multi-step reaction with 8 steps

1: 25 percent / K₂CO₃ / acetone / 6 h / 20 °C

2: molecular sieves 4 Angstroem; N-oxide-N-methylmorpholine; tetra-n-propylammonium perruthenate / CH₂Cl₂ / 1 h / 20 °C

3: 93 percent / CH₂Cl₂ / 48 h / 20 °C

4: 75 percent / NMO; aq. OsO₄ / acetone / 48 h / 20 °C

5: H₂ / Pd/C / methanol / 24 h / 20 °C

6: 1.46 g / NaOMe / methanol / 12 h / Heating

7: 96 percent / H₃B*SMe₂ / tetrahydrofuran / 4 h / 20 °C

8: 73 percent / TBAF*3H₂O / tetrahydrofuran / 12 h / Heating

With osmium(VIII) oxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; dimethylsulfide borane complex; 4 A molecular sieve; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; potassium carbonate; 4-methylmorpholine N-oxide; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1080/07328300600735181

Reference yield:

: (2S,3R,4R,5S)-3,4-Bis-benzyloxy-2-(tert-butyl-diphenyl-silanyloxymethyl)-5-formyl-pyrrolidine-1-carboxylic acid benzyl ester

: 909192-26-3
(1R,2R,3S,6S,7S,7aR)-1,2-dibenzyloxy-6,7-dihydroxy-3-hydroxymethylpyrrolizidine

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / CH₂Cl₂ / 48 h / 20 °C

2: 75 percent / NMO; aq. OsO₄ / acetone / 48 h / 20 °C

3: H₂ / Pd/C / methanol / 24 h / 20 °C

4: 1.46 g / NaOMe / methanol / 12 h / Heating

5: 96 percent / H₃B*SMe₂ / tetrahydrofuran / 4 h / 20 °C

6: 73 percent / TBAF*3H₂O / tetrahydrofuran / 12 h / Heating

With osmium(VIII) oxide; N-methyl-2-indolinone; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; hydrogen; sodium methylate; palladium on activated charcoal; In tetrahydrofuran; methanol; dichloromethane; acetone;
DOI:10.1080/07328300600735181