(2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester

Base Information

• Chemical Name: (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester
• CAS No.: 203449-63-2
• Molecular Formula: C₅₈H₈₈N₂O₁₆Si₂
• Molecular Weight: 1125.51

Synonyms:

Chemical Property of (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester

Chemical Property:

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Technology Process of (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester

There total 1 articles about (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl 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:

(2R,3R)-2,3-Bis-allyloxy-succinic acid dimethyl ester (126863-01-2) + [(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester (161365-25-9) → (2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester (203449-63-2)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate; 9-borabicyclo[3.3.1]nonane dimer; Yield given. Multistep reaction; 1.) THF, 2.) H₂O, DMF;

DOI:10.1016/S0040-4039(97)10616-5

Reference yield:

(2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester (203449-63-2) → (2R,3R)-2,3-Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1,3-bis-(tert-butyl-dimethyl-silanyloxy)-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butoxy)-succinic acid dimethyl ester

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) O₃, DMS, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, 78 deg C, 2.) -78 deg C to RT

2: imidazole / dimethylformamide

With 1H-imidazole; sodium tetrahydroborate; 2,3-dimercapto-succinic acid; ozone; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)10616-5

Reference yield:

(2R,3R)-2,3-Bis-{3-[(3aR,6R,7R,7aR)-6-benzyloxycarbonylamino-7-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,6,7,7a-tetrahydro-benzo[1,3]dioxol-4-yl]-propoxy}-succinic acid dimethyl ester (203449-63-2) → (2R,3R)-2,3-Bis-((S)-4-{(4R,5R)-5-[(1R,2R)-2-benzyloxycarbonylamino-1-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-propyl]-2,2-dimethyl-[1,3]dioxolan-4-yl}-4-hydroxy-butoxy)-succinic acid dimethyl ester

Guidance literature:

With sodium tetrahydroborate; 2,3-dimercapto-succinic acid; ozone; Yield given. Multistep reaction; 1.) CH₂Cl₂, MeOH, 78 deg C, 2.) -78 deg C to RT;

DOI:10.1016/S0040-4039(97)10616-5

upstream raw materials:

(2R,3R)-2,3-Bis-allyloxy-succinic acid dimethyl ester

[(3aR,4R,5R,7aS)-7-Bromo-4-(tert-butyl-dimethyl-silanyloxy)-2,2-dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxol-5-yl]-carbamic acid benzyl ester

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