[(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester
• CAS No.: 102487-60-5
• Molecular Formula: C₁₇H₂₃NO₆
• Molecular Weight: 337.373

Synonyms:[(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

Chemical Property of [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

There total 12 articles about [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-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: 13.0%

Methanesulfonic acid (2R,3R)-3-[(4S,5S)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,3-dihydroxy-propyl ester (102487-59-2) → [(4S,5R)-5-((2R,3S)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester (102518-70-7) + [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester (102487-60-5)

Guidance literature:

With sodium methylate; In methanol; at 20 ℃;

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

Reference yield:

1-O-benzoyl-2,3:5,6-di-O-isopropylidene-D-mannitol (7115-22-2) → [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester (102487-60-5)

Guidance literature:

Multi-step reaction with 10 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: 13 percent / MeONa / methanol / 20 °C

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

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

Reference yield:

2,3,5,6-di-isopropyIidene-1,4-dihydroxy-D-mannitol (3969-61-7) → [(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester (102487-60-5)

Guidance literature:

Multi-step reaction with 11 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: 13 percent / MeONa / methanol / 20 °C

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

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

upstream raw materials:

Methanesulfonic acid (2R,3R)-3-[(4S,5S)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,3-dihydroxy-propyl ester

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

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

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

Downstream raw materials:

[(4S,5R)-5-((2R,3S)-3-Hydroxymethyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

[(4S,5R)-5-((2S,3R)-3-Formyl-oxiranyl)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

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

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

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