[(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester
• CAS No.: 620960-79-4
• Molecular Formula: C₂₅H₄₇NO₆Si₂
• Molecular Weight: 513.822

Synonyms:[(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester

Chemical Property of [(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester

There total 1 articles about [(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl 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: 84.0%

2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone (100776-48-5) → [(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester (620960-79-4)

Guidance literature:

2-(N-benzyloxycarbonyl)-amino-2-deoxy-3,4-di-(tert-butyl-dimethylsilyloxy)-D-arabino-1,4-lactone; With diisobutylaluminium hydride; In dichloromethane;

With sodium tetrahydroborate; In methanol;

DOI:10.1016/j.tetlet.2003.08.105

Reference yield:

[(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester (620960-79-4) → (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 10 steps

1: pyridine / CH₂Cl₂ / 4 h / 20 °C

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

3: H₂ / Pd/C / methanol / 1 h / 20 °C

4: 0.77 g / aq. NaHCO₃ / dioxane / 1 h

5: 77 percent / PPTS / methanol / 0 °C

6: pyridine / 2 h / 0 °C

7: 454 mg / NaN₃ / dimethylformamide / 4 h / 80 °C

8: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

9: 83 percent / TEMPO; KBr; aq. NaClO / NaHCO₃ / acetone / 3 h

10: 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

Reference yield:

[(1R,2S,3R)-2,4-Bis-(tert-butyl-dimethyl-silanyloxy)-3-hydroxy-1-hydroxymethyl-butyl]-carbamic acid benzyl ester (620960-79-4) → (S)-2-[(2S,3S,4R)-2-Amino-5-azido-3,4-bis-(tert-butyl-dimethyl-silanyloxy)-pentanoylamino]-3-(3,5-dibromo-4-hydroxy-phenyl)-propionic acid methyl ester; compound with trifluoro-acetic acid

Guidance literature:

Multi-step reaction with 11 steps

1: pyridine / CH₂Cl₂ / 4 h / 20 °C

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

3: H₂ / Pd/C / methanol / 1 h / 20 °C

4: 0.77 g / aq. NaHCO₃ / dioxane / 1 h

5: 77 percent / PPTS / methanol / 0 °C

6: pyridine / 2 h / 0 °C

7: 454 mg / NaN₃ / dimethylformamide / 4 h / 80 °C

8: 90 percent / DIBAL-H / CH₂Cl₂; toluene / 1 h / -78 °C

9: 83 percent / TEMPO; KBr; aq. NaClO / NaHCO₃ / acetone / 3 h

10: 85 percent / BOP; Et₃N / dimethylformamide / 0 °C

11: CH₂Cl₂ / 1 h / 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

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