(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

Chemical Name:(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
CAS No.:251085-92-4
Molecular Formula:C₂₃H₃₃NO₈
Molecular Weight:451.517
Hs Code.:

(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Synonyms:(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Chemical Property of (2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

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Technology Process of (2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 6 articles about (2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl 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: 97.0%

: 251085-91-3
(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

: 251085-92-4
(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran;
DOI:10.1039/a905310g

Reference yield:

: 123823-24-5
1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose

: 251085-92-4
(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 4 steps

1.1: 87 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

2.1: 62 percent / CrCl₂; NiCl₂; O₂ / dimethylformamide / 25 °C

3.1: BH₃*SMe₂ / tetrahydrofuran / 50 °C

3.2: 57 percent / H₂O₂; NaOH

4.1: 97 percent / Bu₄NF / tetrahydrofuran

With chromium dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; oxygen; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Substitution / 3.1: Addition / 3.2: Oxidation / 4.1: Substitution;
DOI:10.1039/a905310g

Reference yield:

: 33647-85-7
isolevoglucosenone

: 251085-92-4
(2S,4R)-2-[(R)-((1S,2S,3S,4R,5R)-4-Benzyloxy-3-hydroxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yl)-hydroxy-methyl]-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: Et₃N / 25 °C

2.1: 87 percent / LiHMDS / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

3.1: 62 percent / CrCl₂; NiCl₂; O₂ / dimethylformamide / 25 °C

4.1: BH₃*SMe₂ / tetrahydrofuran / 50 °C

4.2: 57 percent / H₂O₂; NaOH

5.1: 97 percent / Bu₄NF / tetrahydrofuran

With chromium dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; oxygen; triethylamine; nickel dichloride; lithium hexamethyldisilazane; In tetrahydrofuran; N,N,N,N,N,N-hexamethylphosphoric triamide; N,N-dimethyl-formamide; 1.1: Addition / 2.1: Substitution / 3.1: Substitution / 4.1: Addition / 4.2: Oxidation / 5.1: Substitution;
DOI:10.1039/a905310g