Benzoic acid, 2-(chloromethyl)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-hydroxy-, (1R)-2-[(2R,3R)-3-ethenyloxiranyl]-1-methylethyl ester

Base Information

• Chemical Name: Benzoic acid, 2-(chloromethyl)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-hydroxy-, (1R)-2-[(2R,3R)-3-ethenyloxiranyl]-1-methylethyl ester
• CAS No.: 378749-94-1
• Molecular Formula: C31H35ClO5Si
• Molecular Weight: 551.154
• Mol file: 378749-94-1.mol

Synonyms:

Chemical Property of Benzoic acid, 2-(chloromethyl)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-hydroxy-, (1R)-2-[(2R,3R)-3-ethenyloxiranyl]-1-methylethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Benzoic acid, 2-(chloromethyl)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-hydroxy-, (1R)-2-[(2R,3R)-3-ethenyloxiranyl]-1-methylethyl ester

There total 10 articles about Benzoic acid, 2-(chloromethyl)-4-[[(1,1-dimethylethyl)diphenylsilyl]oxy]-6-hydroxy-, (1R)-2-[(2R,3R)-3-ethenyloxiranyl]-1-methylethyl 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: 75.0%

(3R,4R,6S)-6-(hydroxy)-3,4-(oxiranyl)hept-1-ene (378749-88-3) + 4-tert-butyldiphenylsiloxy-2-chloromethyl-6-hydroxybenzoic acid (378749-93-0) → 4-(tert-Butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (378749-94-1)

Guidance literature:

With trifuran-2-yl-phosphane; di-isopropyl azodicarboxylate; In benzene;

DOI:10.1002/anie.200390329

Reference yield:

(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-al (378750-01-7) → 4-(tert-Butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (378749-94-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 - 25 °C

1.2: 82 percent / tetrahydrofuran / 0.17 h

2.1: 89 percent / TBAF

3.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C

With di-isopropyl azodicarboxylate; tri(2-furyl) phosphite; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; In tetrahydrofuran; benzene; 3.1: Mitsunobu reaction;

DOI:10.1021/ja011364+

Reference yield:

(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol (328114-40-5) → 4-(tert-Butyl-diphenyl-silanyloxy)-2-chloromethyl-6-hydroxy-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester (378749-94-1)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 90 percent / SO₃*pyridine; Et₃N; DMSO / CH₂Cl₂ / 0 - 25 °C

2.1: NaHMDS / tetrahydrofuran / 0.5 h / 0 - 25 °C

2.2: 82 percent / tetrahydrofuran / 0.17 h

3.1: 89 percent / TBAF

4.1: 75 percent / tri-2-furyl phosphite; DIAD / benzene / 12 h / 25 °C

With pyridine-SO₃ complex; di-isopropyl azodicarboxylate; tri(2-furyl) phosphite; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; benzene; 1.1: Parikh-Doering oxidation / 4.1: Mitsunobu reaction;

DOI:10.1021/ja011364+

upstream raw materials:

(3R,4R,6S)-6-(hydroxy)-3,4-(oxiranyl)hept-1-ene

4-tert-butyldiphenylsiloxy-2-chloromethyl-6-hydroxybenzoic acid

(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-al

(2R,3R,5S)-5-(tert-butyldiphenylsilyl)-2,3-(oxiranyl)hexan-1-ol

Downstream raw materials:

4-(tert-Butyl-diphenyl-silanyloxy)-2-hydroxy-6-[((1E,3E)-2-penta-1,3-dienyl)-[1,3]dithian-2-ylmethyl]-benzoic acid (R)-1-methyl-2-((2R,3R)-3-vinyl-oxiranyl)-ethyl ester

Monocillin I

(9Z,11E)-(4R,6R,8R)-16-Chloro-17,19-dihydroxy-4-methyl-3,7-dioxa-tricyclo[13.4.0.0^6,8]nonadeca-1⁽¹⁵⁾,9,11,16,18-pentaene-2,13-dione

C₄₃H₅₆O₅S₂Si₂