(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

Base Information

Chemical Name:(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol
CAS No.:1388144-86-2
Molecular Formula:C₃₀H₄₄O₄Si
Molecular Weight:496.762
Hs Code.:

Synonyms:(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

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Chemical Property of (S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

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Technology Process of (S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

There total 9 articles about (S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol 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:

: 1388144-80-6
((R)-6-(4-methoxybenzyloxy)hexan-2-yloxy)(tert-butyl)diphenylsilane

: 1388144-86-2
(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

Guidance literature:: Multi-step reaction with 7 steps

1.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

2.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

2.2: -78 - 20 °C

3.1: sodium hydride / diethyl ether; mineral oil / 0.17 h / -5 °C

3.2: 4 h / -5 - 20 °C

4.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol

5.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

7.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane / 72 h / -78 - -20 °C / Molecular sieve

7.2: 1 h

With titanium(IV) isopropylate; oxalyl dichloride; methanesulfonamide; AD-mix-β; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol; 2.1: Swern oxidation / 2.2: Swern oxidation / 3.2: Horner-Wadsworth-Emmons olefination / 4.1: Sharpless dihydroxylation / 7.1: Keck allylation;
DOI:10.1016/j.tetasy.2012.05.017

Reference yield:

: 1388144-81-7
(R,E)-ethyl 7-tert-butyldiphenylsilanyloxyoct-2-enoate

: 1388144-86-2
(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

Guidance literature:: Multi-step reaction with 4 steps

1.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol

2.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

4.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane / 72 h / -78 - -20 °C / Molecular sieve

4.2: 1 h

With titanium(IV) isopropylate; methanesulfonamide; AD-mix-β; (S)-[1,1']-binaphthalenyl-2,2'-diol; diisobutylaluminium hydride; toluene-4-sulfonic acid; In dichloromethane; water; toluene; tert-butyl alcohol; 1.1: Sharpless dihydroxylation / 4.1: Keck allylation;
DOI:10.1016/j.tetasy.2012.05.017

Reference yield:

: 131375-69-4
5-((4-methoxybenzyl)oxy)pentanal

: 1388144-86-2
(S)-1-((4R,5R)-5-((R)-4-(tert-butyldiphenylsilanyloxy)pentyl)-2,2-dimethyl-1,3-dioxolan-4-yl)but-3-en-1-ol

Guidance literature:: Multi-step reaction with 11 steps

1.1: magnesium / diethyl ether / Reflux

1.2: 2 h / -78 - 20 °C

1.3: Cooling

2.1: chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); potassium tert-butylate; sodium carbonate / toluene / 6 h / 20 °C / Inert atmosphere

3.1: methanol; potassium carbonate / 2 h / 20 °C

4.1: 1H-imidazole / dichloromethane / 20 °C

5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane; water / 1 h / 20 °C

6.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 0.75 h / -78 °C

6.2: -78 - 20 °C

7.1: sodium hydride / diethyl ether; mineral oil / 0.17 h / -5 °C

7.2: 4 h / -5 - 20 °C

8.1: AD-mix-β; methanesulfonamide / water; tert-butyl alcohol

9.1: toluene-4-sulfonic acid / dichloromethane / 1 h / 20 °C

10.1: diisobutylaluminium hydride / dichloromethane; toluene / 1 h / -78 °C

11.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / dichloromethane / 72 h / -78 - -20 °C / Molecular sieve

11.2: 1 h

With 1H-imidazole; titanium(IV) isopropylate; methanol; chlorodicarbonyl(1-(isopropylamino)-2,3,4,5-tetraphenylcyclopentadienyl) ruthenium (II); oxalyl dichloride; methanesulfonamide; AD-mix-β; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; sodium hydride; diisobutylaluminium hydride; sodium carbonate; potassium carbonate; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In diethyl ether; dichloromethane; water; toluene; mineral oil; tert-butyl alcohol; 6.1: Swern oxidation / 6.2: Swern oxidation / 7.2: Horner-Wadsworth-Emmons olefination / 8.1: Sharpless dihydroxylation / 11.1: Keck allylation;
DOI:10.1016/j.tetasy.2012.05.017