(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Base Information

Chemical Name:(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester
CAS No.:863453-40-1
Molecular Formula:C₃₂H₄₄O₈S
Molecular Weight:588.763
Hs Code.:

Synonyms:(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Suppliers and Price of (E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

There total 11 articles about (E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl 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: 98.0%

: 863453-53-6
(E)-(2S,3S)-2-Benzyloxy-3-((4S,5R)-5-hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-4,8-dimethyl-non-4-enoic acid methyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 863453-40-1
(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: With pyridine; In dichloromethane; at 4 ℃; for 20h;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: 863453-34-3
(E)-3-((4S,5R)-5-Hydroxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-2-methyl-acrylic acid methyl ester

: 863453-40-1
(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: 95 percent / imidazole / dimethylformamide / 3 h / 20 °C

2.1: 96 percent / DIBAL-H / CH₂Cl₂ / 4 h / -78 °C

3.1: 91 percent / MnO₂ / CH₂Cl₂ / 20 h / 20 °C

4.1: 25 percent / tetrahydrofuran / 1 h / -78 °C

5.1: 82 percent / PPh₃; DIAD / tetrahydrofuran / 3.5 h / 0 - 20 °C

6.1: LiHMDS; TMSCl; Et₃N / tetrahydrofuran / 11 h / -78 - 20 °C

6.2: 70 percent / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

7.1: 80 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

8.1: 98 percent / pyridine / CH₂Cl₂ / 20 h / 4 °C

With pyridine; 1H-imidazole; manganese(IV) oxide; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 5.1: Mitsunobu reaction / 6.1: Ireland-Claisen rearrangement;
DOI:10.1016/j.bmcl.2005.05.065

Reference yield:

: 863453-35-4
(E)-3-[(4S,5R)-5-(tert-Butyl-diphenyl-silanyloxymethyl)-2,2-dimethyl-[1,3]dioxolan-4-yl]-2-methyl-propenal

: 863453-40-1
(E)-(2S,3S)-2-Benzyloxy-3-[(4S,5R)-2,2-dimethyl-5-(toluene-4-sulfonyloxymethyl)-[1,3]dioxolan-4-yl]-4,8-dimethyl-non-4-enoic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1.1: 25 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 82 percent / PPh₃; DIAD / tetrahydrofuran / 3.5 h / 0 - 20 °C

3.1: LiHMDS; TMSCl; Et₃N / tetrahydrofuran / 11 h / -78 - 20 °C

3.2: 70 percent / tetrahydrofuran; diethyl ether / 0.08 h / 0 °C

4.1: 80 percent / TBAF / tetrahydrofuran / 12 h / 20 °C

5.1: 98 percent / pyridine / CH₂Cl₂ / 20 h / 4 °C

With pyridine; chloro-trimethyl-silane; di-isopropyl azodicarboxylate; tetrabutyl ammonium fluoride; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; 2.1: Mitsunobu reaction / 3.1: Ireland-Claisen rearrangement;
DOI:10.1016/j.bmcl.2005.05.065