Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Base Information

• Chemical Name: Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester
• CAS No.: 279684-80-9
• Molecular Formula: C₃₇H₆₆O₇Si₃
• Molecular Weight: 707.183
• Mol file: 279684-80-9.mol

Synonyms:Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Chemical Property of Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester

There total 10 articles about Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl 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: 83.0%

3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol (279684-76-3) + (2R,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yne-2,3-diol 2-benzoate ester (279684-79-6) → Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester (279684-80-9)

Guidance literature:

With camphor-10-sulfonic acid; In toluene; at 20 ℃; for 12h;

DOI:10.1021/ja994229u

Reference yield:

(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one (53723-96-9) → Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester (279684-80-9)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / BH₃-SMe₂; (R)-2-methyl-CBS-oxazaborolidine / tetrahydrofuran / 3.5 h / -45 °C

2: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

3: 100 percent / Ti(O-i-Pr)4 / benzene / 0.5 h / 70 °C

4: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

5: 83 percent / imidazole / dimethylformamide / 1 h / 20 °C

6: 83 percent / CSA / toluene / 12 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; dimethylsulfide borane complex; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Reduction / 2: Epoxidation / 3: Addition / 4: desilylation / 5: silylation / 6: glycosylation;

DOI:10.1021/ja994229u

Reference yield:

(R)-1-(trimethylsilyl)hex-4-en-1-yn-3-ol → Benzoic acid (1R,2R,3S)-2-[(2S,4S,5R,6R)-4,5-bis-(tert-butyl-dimethyl-silanyloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-3-(tert-butyl-dimethyl-silanyloxy)-1-methyl-pent-4-ynyl ester (279684-80-9)

Guidance literature:

Multi-step reaction with 5 steps

1: 76 percent / cumene hydroperoxide; Ti(O-i-Pr)4; L-(+)-diisopropyl tartrate / CH₂Cl₂ / 5.5 h / -30 °C

2: 100 percent / Ti(O-i-Pr)4 / benzene / 0.5 h / 70 °C

3: 100 percent / Bu₄NF / tetrahydrofuran / 0.5 h / 20 °C

4: 83 percent / imidazole / dimethylformamide / 1 h / 20 °C

5: 83 percent / CSA / toluene / 12 h / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; L-(+)-diisopropyl tartrate; Cumene hydroperoxide; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 1: Epoxidation / 2: Addition / 3: desilylation / 4: silylation / 5: glycosylation;

DOI:10.1021/ja994229u

upstream raw materials:

3,4-bis-(tert-butyldimethylsilyl)-1,5-anhydro-2,6-dideoxy-D-ribo-hex-1-enitol

(2R,3R,4S)-4-(tert-butyldimethylsiloxy)-hex-5-yne-2,3-diol 2-benzoate ester

tert-butyldimethylsilyl chloride

(2E)-6-(trimethylsilyl)hex-2-en-5-yn-4-one

Downstream raw materials:

Benzoic acid (1R,2R,3S)-3-(tert-butyl-dimethyl-silanyloxy)-2-[(2S,4S,5R,6R)-4-(tert-butyl-dimethyl-silanyloxy)-5-((2S,4S,5R,6R)-4,5-diacetoxy-6-methyl-tetrahydro-pyran-2-yloxy)-6-methyl-tetrahydro-pyran-2-yloxy]-1-methyl-pent-4-ynyl ester

digitoxin

Refernces

• 1、 McDonald, Frank E.,Reddy, K. Subba,Diaz, Yolanda. "Stereoselective glycosylations of a family of 6-deoxy-1,2-glycals generated by catalytic alkynol cycloisomerization". . p. 4304 - 4309. Retrieved 2007/10/03.