((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Base Information

• Chemical Name: ((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester
• CAS No.: 104241-40-9
• Molecular Formula: C₁₁H₁₉NO₅
• Molecular Weight: 245.276

Synonyms:((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Chemical Property of ((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

Chemical Property:

Purity/Quality:

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Technology Process of ((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester

There total 1 articles about ((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic 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: 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:

((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (104241-40-9) → (2S,4R)-(linoleyl)amino-4-(tert-butyldimethylsilyl)oxy-5-dimethoxypentanoyl-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 amide

Guidance literature:

Multi-step reaction with 11 steps

1: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

2: diethyl ether

3: pyridine / 8 h / Ambient temperature

4: 62 percent / NaH / tetrahydrofuran / 1.5 h / 0 °C

5: CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

6: diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 15 h / 0 °C

8: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

9: 38 percent / NH₃(g) / methanol / 132 h / Ambient temperature

10: 100 percent / H₂ / 10percent Pd-C / ethanol / 14 h / Ambient temperature

11: 56 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) DMF, 0 deg C, 4.5 h, 2) RT, 20 h

With pyridine; sodium hydroxide; diethylphosphoryl cyanide; ammonia; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

((3S,4S,5S)-4-Hydroxy-5-methyl-2-oxo-tetrahydro-pyran-3-yl)-carbamic acid tert-butyl ester (104241-40-9) → C36H59N5O12Si

Guidance literature:

Multi-step reaction with 9 steps

1: 0.5 NaOH / tetrahydrofuran / 16 h / 0 °C

2: diethyl ether

3: pyridine / 8 h / Ambient temperature

4: 62 percent / NaH / tetrahydrofuran / 1.5 h / 0 °C

5: CF₃COOH / CH₂Cl₂ / 0.5 h / Ambient temperature

6: diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 15 h / 0 °C

8: 72 percent / diethylphosphoryl cyanide, NEt₃ / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 2 h

9: 100 percent / H₂ / 10percent Pd-C / methanol / 32 h / 760 Torr / Ambient temperature

With pyridine; sodium hydroxide; diethylphosphoryl cyanide; hydrogen; sodium hydride; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

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

Downstream raw materials:

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

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 amide

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