(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one

Base Information

• Chemical Name: (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one
• CAS No.: 286933-02-6
• Molecular Formula: C₂₃H₃₇NO₃Si
• Molecular Weight: 403.637
• Mol file: 286933-02-6.mol

Synonyms:(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one

Chemical Property of (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one

There total 1 articles about (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one 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: 56.0%

N-(p-methoxyphenyl)pent-4-enaldimine (286933-13-9) + (1R,2S)-2-phenyl-1-cyclohexyl<(triisopropylsilyl)oxy>acetate (132127-27-6) → (3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one (286933-02-6)

Guidance literature:

(1R,2S)-2-phenyl-1-cyclohexyl<(triisopropylsilyl)oxy>acetate; With n-butyllithium; diisopropylamine; In tetrahydrofuran; hexane; at -84 ℃;

N-(p-methoxyphenyl)pent-4-enaldimine; In tetrahydrofuran; at -84 - 20 ℃; Further stages.;

DOI:10.1021/ja000293w

Reference yield:

(3R,4S)-1-(4-methoxyphenyl)-3-triisopropylsiloxy-4-(3-butenyl)azetidin-2-one (286933-02-6) → 2-debenzoyl-2-(2-allyloxybenzoyl)-7-triethylsilyl-13-[(2R,3S)-3-tert-butoxycarbonylamino-2-triethylsiloxyhept-6-enoyl]baccatin III (237762-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1.1: ceric ammonium nitrate / acetonitrile; H₂O

1.2: Et₃N / DMAP / CH₂Cl₂

2.1: HF; pyridine / acetonitrile / 20 °C

3.1: DMAP; Et₃N / CH₂Cl₂ / 20 °C

4.1: 64 percent / LiHMDS / tetrahydrofuran / -40 °C

With pyridine; dmap; ammonium cerium(IV) nitrate; hydrogen fluoride; triethylamine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile; 1.1: oxidative cleavage / 1.2: Acylation / 2.1: desilylation / 3.1: silylation / 4.1: Acylation;

DOI:10.1021/ja000293w

upstream raw materials:

N-(p-methoxyphenyl)pent-4-enaldimine

(1R,2S)-2-phenyl-1-cyclohexyl<(triisopropylsilyl)oxy>acetate

Downstream raw materials:

2-debenzoyl-2-(2-allyloxybenzoyl)-7-triethylsilyl-13-[(2R,3S)-3-tert-butoxycarbonylamino-2-triethylsiloxyhept-6-enoyl]baccatin III