3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester

Base Information

• Chemical Name: 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester
• CAS No.: 102487-63-8
• Molecular Formula: C₂₉H₄₇NO₈Si
• Molecular Weight: 565.78
• Mol file: 102487-63-8.mol

Synonyms:

Chemical Property of 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester

There total 16 articles about 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic 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:

1-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannitol (7115-22-2) → 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester (102487-63-8,102505-11-3,107025-32-1,107025-33-2)

Guidance literature:

Multi-step reaction with 13 steps

1: imidazole / dimethylformamide / 80 °C

2: 1N NaOH / methanol / Ambient temperature

3: 91 percent / DMSO/DCC/TFA / pyridine; benzene / Ambient temperature

4: 87 percent / K₂CO₃ / methanol / Ambient temperature

5: 99 percent / H₂NOH_.HCl, NaHCO₃ / ethanol; H₂O / 60 °C

6: LiAlH₄ / tetrahydrofuran / Ambient temperature

7: tetrahydrofuran; H₂O / 0 °C

8: 21 percent / TsOH / methanol; H₂O / 15 °C

9: 68 percent / pyridine / 5 °C

10: 60 percent / MeONa / methanol / 20 °C

11: CrO_3.2 pyridine / CH₂Cl₂ / 5 °C

12: 24 percent

13: imidazole / dimethylformamide / 80 °C

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; sodium methylate; dipyridine chromium trioxide; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)98767-7

Reference yield:

2,3:5,6-Di-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-aldehydo-D-glucose (102487-54-7) → 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester (102487-63-8,102505-11-3,107025-32-1,107025-33-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 99 percent / H₂NOH_.HCl, NaHCO₃ / ethanol; H₂O / 60 °C

2: LiAlH₄ / tetrahydrofuran / Ambient temperature

3: tetrahydrofuran; H₂O / 0 °C

4: 21 percent / TsOH / methanol; H₂O / 15 °C

5: 68 percent / pyridine / 5 °C

6: 60 percent / MeONa / methanol / 20 °C

7: CrO_3.2 pyridine / CH₂Cl₂ / 5 °C

8: 24 percent

9: imidazole / dimethylformamide / 80 °C

With 1H-imidazole; lithium aluminium tetrahydride; hydroxylamine hydrochloride; sodium methylate; dipyridine chromium trioxide; sodium hydrogencarbonate; toluene-4-sulfonic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(00)98767-7

Reference yield:

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol (3969-61-7) → 3-{(2R,3R)-3-[(4R,5S)-5-(Benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-oxiranyl}-3-(tert-butyl-dimethyl-silanyloxy)-propionic acid tert-butyl ester (102487-63-8,102505-11-3,107025-32-1,107025-33-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 62 percent / pyridine / Ambient temperature

2: imidazole / dimethylformamide / 80 °C

3: 1N NaOH / methanol / Ambient temperature

4: 91 percent / DMSO/DCC/TFA / pyridine; benzene / Ambient temperature

5: 87 percent / K₂CO₃ / methanol / Ambient temperature

6: 99 percent / H₂NOH_.HCl, NaHCO₃ / ethanol; H₂O / 60 °C

7: LiAlH₄ / tetrahydrofuran / Ambient temperature

8: tetrahydrofuran; H₂O / 0 °C

9: 21 percent / TsOH / methanol; H₂O / 15 °C

10: 68 percent / pyridine / 5 °C

11: 60 percent / MeONa / methanol / 20 °C

12: CrO_3.2 pyridine / CH₂Cl₂ / 5 °C

13: 24 percent

14: imidazole / dimethylformamide / 80 °C

With pyridine; 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; sodium methylate; dipyridine chromium trioxide; sodium hydrogencarbonate; potassium carbonate; toluene-4-sulfonic acid; dimethyl sulfoxide; dicyclohexyl-carbodiimide; trifluoroacetic acid; In tetrahydrofuran; pyridine; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4039(00)98767-7

upstream raw materials:

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol

1-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannitol

t-butyl lithioacetate

2,3:5,6-Di-O-isopropylidene-4-O-(tert-butyldimethylsilyl)-aldehydo-D-glucose