2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester

Base Information

• Chemical Name: 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester
• CAS No.: 620960-80-7
• Molecular Formula: C₃₀H₅₅NO₇Si₂
• Molecular Weight: 597.94
• Mol file: 620960-80-7.mol

Synonyms:2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester

Chemical Property of 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester

There total 1 articles about 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl 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:

2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5) → 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester (620960-80-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

1.2: 84 percent / NaBH₄ / methanol / 0.5 h / 20 °C

2.1: pyridine / CH₂Cl₂ / 4 h / 20 °C

With pyridine; diisobutylaluminium hydride; In dichloromethane; toluene;

DOI:10.1016/j.tet.2004.04.062

Reference yield: 85.0%

t-butyldimethylsiyl triflate (69739-34-0) + 2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester (620960-80-7) → 2-(N-benzyloxycarbonyl)amino-2-deoxy-3,4,5-tri(tert-butyldimethylsilyloxy)-1-pivaloyl-D-arabinitol (620960-81-8)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane;

DOI:10.1016/j.tetlet.2003.08.105

Reference yield:

2,2-Dimethyl-propionic acid (2R,3S,4R)-2-benzyloxycarbonylamino-3,5-bis-(tert-butyl-dimethyl-silanyloxy)-4-hydroxy-pentyl ester (620960-80-7) → (S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester (620960-65-8)

Guidance literature:

Multi-step reaction with 9 steps

1: 398 mg / 2,6-lutidine / CH₂Cl₂ / 1 h

2: H₂ / Pd/C / methanol / 1 h / 20 °C

3: 0.77 g / aq. NaHCO₃ / dioxane / 1 h

4: 77 percent / PPTS / methanol / 0 °C

5: pyridine / 2 h / 0 °C

6: 454 mg / NaN₃ / dimethylformamide / 4 h / 80 °C

7: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

8: 83 percent / TEMPO; KBr; aq. NaClO / NaHCO₃ / acetone / 3 h

9: 85 percent / BOP; Et₃N / dimethylformamide / 0 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; sodium hypochlorite; sodium azide; hydrogen; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; sodium hydrogencarbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; triethylamine; potassium bromide; palladium on activated charcoal; sodium hydrogencarbonate; In 1,4-dioxane; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene;

DOI:10.1016/j.tet.2004.04.062

upstream raw materials:

2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone

Downstream raw materials:

2-(N-benzyloxycarbonyl)amino-2-deoxy-3,4,5-tri(tert-butyldimethylsilyloxy)-1-pivaloyl-D-arabinitol

(S)-2-[(2S,3S,4R)-5-Azido-2-tert-butoxycarbonylamino-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester

(S)-2-[(2S,3S,4R)-5-Azido-2-[(S)-2-tert-butoxycarbonylamino-3-(4-hydroxy-3,5-diiodo-phenyl)-propionylamino]-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester