(2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Base Information

• Chemical Name: (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate
• CAS No.: 106074-85-5
• Molecular Formula: C₂₈H₄₇NO₇Si
• Molecular Weight: 537.769

Synonyms:(2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Chemical Property of (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

There total 7 articles about (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate 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: 98.0%

3,4-dihydro-2H-pyran (110-87-2) + (2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (104241-27-2) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (106074-85-5)

Guidance literature:

With camphor-10-sulfonic acid; In dichloromethane; at 0 ℃; for 1.5h;

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

Reference yield:

4-bromo-phenol (106-41-2) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (106074-85-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / imidazole / dimethylformamide / 1) 0 deg C, 1 h, 2) RT, 30 min

3: 98 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 °C

With 1H-imidazole; camphor-10-sulfonic acid; In dichloromethane; N,N-dimethyl-formamide;

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

Reference yield:

t-butyldimethylsilyl-4-bromophenol (67963-68-2) → (2R,3R)-2-(tert-butoxycarbonyl)amino-3-(tetrahydropyranyl)oxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate (106074-85-5)

Guidance literature:

Multi-step reaction with 2 steps

2: 98 percent / dl-10-camphorsulfonic acid / CH₂Cl₂ / 1.5 h / 0 °C

With camphor-10-sulfonic acid; In dichloromethane;

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

upstream raw materials:

3,4-dihydro-2H-pyran

(2R,3R)-2-(tert-butoxycarbonyl)amino-3-hydroxy-4-<4-(tert-butyldimethylsilyl)oxy>phenylbutyl acetate

4-bromo-phenol

t-butyldimethylsilyl-4-bromophenol

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 amide

echinocandin D

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

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

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