(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

Base Information

Chemical Name:(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol
CAS No.:536737-60-7
Molecular Formula:C₂₆H₅₄O₅Si₂
Molecular Weight:502.883
Hs Code.:

Synonyms:(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

Suppliers and Price of (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

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 (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

There total 1 articles about (3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-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:

: 80522-42-5
triisopropylsilyl trifluoromethanesulfonate

: 536737-60-7
(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

Guidance literature:: Multi-step reaction with 9 steps

1: 90 percent / DIBAL / -78 °C

2: 80 percent / (+)-DIPT; Ti(O-i-Pr)4; TBHP / MS 4 Angstroem / CH₂Cl₂ / 6 h / -20 °C

3: TPAP; NMO; MS 4 Angstroem / CH₂Cl₂ / 0.5 h / 20 °C

4: 837 mg / tetrahydrofuran / 0.5 h / -20 °C

5: 99 percent / 2,6-lutidine / CH₂Cl₂ / 0.5 h / -20 °C

6: 93 percent / TiCl₄ / CH₂Cl₂ / 0.33 h / -78 °C

7: 82 percent / HCl; ethylene glycol / diethyl ether; tetrahydrofuran

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; tert.-butylhydroperoxide; N-methyl-2-indolinone; tetrapropylammonium perruthennate; L-(+)-diisopropyl tartrate; MS 4 Angstroem; titanium tetrachloride; diisobutylaluminium hydride; ethylene glycol; MS 4 Angstroem; In tetrahydrofuran; diethyl ether; dichloromethane; 4: Sharpless asymmetric epoxidation / 8: Tsuchihashi-Suzuki rearrangement;
DOI:10.1021/ja034332q

Reference yield: 82.0%

: 824-94-2
p-methoxybenzyl chloride

: 536737-60-7
(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

: 164364-98-1
(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-(4-methoxybenzyloxy)-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene

Guidance literature:: With potassium hydride; In tetrahydrofuran; for 2h; Heating;
DOI:10.1021/ja034332q

Reference yield:

: 536737-60-7
(3S,4R,5R)-2,3-dimethyl-3-(1,3-dioxolan-2-yl)-4-hydroxy-5-(tert-butyldimethylsiloxy)-6-(triisopropylsiloxy)-1-hexene-4-ol

: (2S,3R,4R,5R)-3-[(2R,3R)-2,3-dihydroxy-2-pentyl]-5-(triisopropylsiloxymethyl)-2-methoxy-4-(4-methoxybenzyloxy)-3-methyloxolane

Guidance literature:: Multi-step reaction with 7 steps

1: 82 percent / KH / tetrahydrofuran / 2 h / Heating

2: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2 h / 20 °C

3: 84 percent / HCl / diethyl ether / 2 h / 20 °C

4: 98 percent / DMAP; imidazole / CH₂Cl₂ / 20 °C

5: 85 percent / NMO; aq. OsO₄ / acetone / 4 h / 20 °C

6: DMSO; oxalyl chloride; triethylamine / CH₂Cl₂ / -78 - 0 °C

7: tetrahydrofuran / 0.5 h / 20 °C

With 1H-imidazole; hydrogenchloride; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; tetrabutyl ammonium fluoride; potassium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; 6: Swern oxidation;
DOI:10.1021/ja034332q