(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Base Information

Chemical Name:(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol
CAS No.:792921-80-3
Molecular Formula:C₃₃H₄₄O₃Si
Molecular Weight:516.796
Hs Code.:

Synonyms:(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Suppliers and Price of (3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Supply Marketing:

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

Manufacturers and distributors:

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Chemicals and raw materials
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Total 3 raw suppliers

Chemical Property of (3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Chemical Property:

Purity/Quality:: 98% ^*data from raw suppliers

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

There total 15 articles about (3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-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:

: 792921-79-0
(4R,5S,2E)-5,7-bis(tert-butyldimethylsilyloxy)-4-methylhept-2-en-1-ol

: 792921-80-3
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 100 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

2: 89 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

With pyridine; dmap; pyridine hydrogenfluoride; In tetrahydrofuran;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 792921-70-1
ethyl (4R,5S,2E)-5,7-bis(tert-butyldimethylsilyloxy)-4-methylhept-2-enoate

: 792921-80-3
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Guidance literature:: Multi-step reaction with 3 steps

1: 97 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 °C

2: 100 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

3: 89 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

With pyridine; dmap; diisobutylaluminium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; hexane; dichloromethane;
DOI:10.1016/j.tet.2007.05.033

Reference yield:

: 219606-81-2
(3R,4S)-4,6-bis(tert-butyldimethylsilyloxy)-3-methylhex-1-ene

: 792921-80-3
(3S,4R,5E)-3-(tert-butyldimethylsilyloxy)-4-methyl-7-(trityloxy)hept-5-en-1-ol

Guidance literature:: Multi-step reaction with 6 steps

1.1: OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 0.17 h / 20 °C

1.2: NMO / acetone; H₂O; 2-methyl-propan-2-ol / 23 h / 20 °C

2.1: NaIO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 4 h

3.1: NaH / tetrahydrofuran / -5 - 20 °C

3.2: 1.00 g / tetrahydrofuran / 2 h / 0 °C

4.1: 97 percent / diisobutylaluminum hydride / hexane; CH₂Cl₂ / -78 °C

5.1: 100 percent / 4-(dimethylamino)pyridine; pyridine / 18 h / Heating

6.1: 89 percent / HF*pyridine complex; pyridine / tetrahydrofuran / 20 °C

With pyridine; dmap; sodium periodate; osmium(VIII) oxide; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; In tetrahydrofuran; hexane; dichloromethane; water; acetone; tert-butyl alcohol; 3.2: Horner-Wadsworth-Emmons reaction;
DOI:10.1016/j.tet.2007.05.033