(2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester

Base Information

• Chemical Name: (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester
• CAS No.: 104241-25-0
• Molecular Formula: C₁₉H₂₉NO₈S
• Molecular Weight: 431.507

Synonyms:(2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester

Chemical Property of (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester

There total 6 articles about (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl 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: 45.3%

(2S,3S,4S)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-methyl-5-benzyloxypentanoic acid methyl ester (104241-23-8) → ((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (104241-40-9) + (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester (104241-25-0)

Guidance literature:

With hydrogen; palladium on activated charcoal; In methanol; for 20h; Yields of byproduct given; Ambient temperature;

DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

(2S,3S,4S)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-methyl-5-benzyloxypentanoic acid methyl ester (104241-23-8) → (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester (104241-25-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 45.3 percent / H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

2: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

3: diethyl ether

4: pyridine / 8 h / Ambient temperature

With pyridine; sodium hydroxide; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether;

DOI:10.1016/S0040-4020(01)87959-X

Reference yield:

(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol (81520-04-9) → (2S,3S,4S)-2-(tert-butoxycarobnyl)amino-3-hydroxy-4-methyl-5-(p-toluenesulfonyl)oxypentanoic acid methyl ester (104241-25-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 79 percent / pyridinium dichromate / dimethylformamide / 45 h / Ambient temperature

2: 72 percent / 28percent aq. NH₃ / 120 h / Ambient temperature

3: NEt₃ / dioxane; H₂O / 4 h / Ambient temperature

4: diethyl ether

5: 45.3 percent / H₂ / 10percent Pd-C / methanol / 20 h / Ambient temperature

6: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

7: diethyl ether

8: pyridine / 8 h / Ambient temperature

With pyridine; ammonium hydroxide; sodium hydroxide; dipyridinium dichromate; hydrogen; triethylamine; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; water; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(01)87959-X

upstream raw materials:

p-toluenesulfonyl chloride

(2S,3S,4S)-2-tert-Butoxycarbonylamino-3,5-dihydroxy-4-methyl-pentanoic acid methyl ester

(2S,3S,4S)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-methyl-5-benzyloxypentanoic acid methyl ester

(2S,3S,4S)-5-(benzyloxy)-2,3-epoxy-4-methyl-1-pentanol

Downstream raw materials:

N^α-linoleyl-N^δ-(tert-butoxycarbonyl)-L-ornithinyl-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

N-(benzyloxycarbonyl)-O-(tert-butyldimethylsilyl)-L-threonyl-4(R)-hydroxy-L-prolyl-3(R)-hydroxy-L-homotyrosinyl-L-threonyl-3(S)-hydroxy-4(S)-methyl-L-proline methyl ester

echinocandin D

(2S,3S,4S)-3-Hydroxy-4-methyl-pyrrolidine-2-carboxylic acid methyl ester

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