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

Base Information

• Chemical Name: Methanesulfonic acid (2R,3R)-3-[(4S,5S)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,3-dihydroxy-propyl ester
• CAS No.: 102487-59-2
• Molecular Formula: C₁₈H₂₇NO₉S
• Molecular Weight: 433.48

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

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

Chemical Property:

Purity/Quality:

Safty Information:

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

There total 11 articles about Methanesulfonic acid (2R,3R)-3-[(4S,5S)-5-(benzyloxycarbonylamino-methyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2,3-dihydroxy-propyl 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: 68.0%

[(4S,5S)-2,2-Dimethyl-5-((1R,2R)-1,2,3-trihydroxy-propyl)-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester (102487-58-1) + methanesulfonyl chloride (124-63-0) → 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)

Guidance literature:

In pyridine; at 5 ℃;

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) → 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)

Guidance literature:

Multi-step reaction with 9 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

With 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; 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) → 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)

Guidance literature:

Multi-step reaction with 10 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

With pyridine; 1H-imidazole; sodium hydroxide; lithium aluminium tetrahydride; hydroxylamine hydrochloride; 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:

[(4S,5S)-2,2-Dimethyl-5-((1R,2R)-1,2,3-trihydroxy-propyl)-[1,3]dioxolan-4-ylmethyl]-carbamic acid benzyl ester

methanesulfonyl chloride

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

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

Downstream raw materials:

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

[(4S,5S)-5-((R)-Hydroxy-(R)-oxiranyl-methyl)-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

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