(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

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-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 251085-91-3
• Molecular Formula: C₂₉H₄₇NO₈Si
• Molecular Weight: 565.78
• Mol file: 251085-91-3.mol

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-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

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-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 5 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-(tert-butyl-dimethyl-silanyloxy)-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: 57.0%

(2S,4R)-2-[(R)-((1S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-en-2-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester (251085-89-9) → (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 (251085-91-3)

Guidance literature:

(2S,4R)-2-[(R)-((1S,4R,5R)-4-Benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-en-2-yl)-hydroxy-methyl]-4-(tert-butyl-dimethyl-silanyloxy)-pyrrolidine-1-carboxylic acid tert-butyl ester; With dimethylsulfide borane complex; In tetrahydrofuran; at 50 ℃;

With sodium hydroxide; dihydrogen peroxide;

DOI:10.1039/a905310g

Reference yield:

isolevoglucosenone (33647-85-7) → (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 (251085-91-3)

Guidance literature:

Multi-step reaction with 4 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

With chromium dichloride; dimethylsulfide borane complex; 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;

DOI:10.1039/a905310g

Reference yield:

1,6-anhydro-2-O-benzyl-3-deoxy-β-D-erythro-hexopyrano-4-ulose (123823-24-5) → (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 (251085-91-3)

Guidance literature:

Multi-step reaction with 3 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

With chromium dichloride; dimethylsulfide borane complex; 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;

DOI:10.1039/a905310g

upstream raw materials:

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

isolevoglucosenone

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

(1R,4R,5R)-4-benzyloxy-6,8-dioxabicyclo[3.2.1]oct-2-en-2-yl trifluoromethanesulfonate

Downstream raw materials:

(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