(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Base Information

Chemical Name:(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester
CAS No.:511256-89-6
Molecular Formula:C₂₉H₄₇F₃O₉SSi
Molecular Weight:656.833
Hs Code.:

(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Synonyms:(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Suppliers and Price of (2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl 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 (2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

There total 20 articles about (2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl 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: 92.0%

: 69739-34-0
t-butyldimethylsiyl triflate

: 511256-98-7
Trifluoro-methanesulfonic acid (2R,3S,4aR,6S,7R,8aS)-3,7-dihydroxy-6-[3-(4-methoxy-benzyloxy)-propyl]-7,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-2-ylmethyl ester

: 511256-89-6
(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: With 2,6-dimethylpyridine; In dichloromethane; at 0 ℃; for 3h;
DOI:10.1021/ol034100w

Reference yield:

: 511256-86-3
(4aR,6S,7R,8aS)-2,2-di(tert-butyl)-7-{1-[3-(4-methoxybenzyloxy)propyl]vinyloxy}-6-methyl-6-(2-methylallyl)-4,4a,6,7,8,8a-hexahydro-1,3,5-trioxa-2-silanaphthalene

: 511256-89-6
(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 6 steps

1: 83 percent / PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 80 °C

2: dimethyldioxirane

3: DIBAL-H

4: 100 percent / HF*pyridine / tetrahydrofuran / 0 °C

5: 2,6-lutidine / CH₂Cl₂ / -65 °C

6: 2,6-lutidine / 0 °C

With 2,6-dimethylpyridine; 3,3-dimethyldioxirane; diisobutylaluminium hydride; pyridine hydrogenfluoride; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; dichloromethane; benzene;
DOI:10.1002/chem.200500993

Reference yield:

: 191593-14-3
4,6-O-di(tert-butyl)silanediyl-D-glucal

: 511256-89-6
(2R,3S,4aR,6R,7R,8aR,9aS,10aS)-trifluoromethanesulfonic acid 3-(tert-butyldimethylsilanyloxy)-7-hydroxy-6-[3-(4-methoxybenzyloxy)propyl]-7,8a-dimethyloctahydropyrano[3,2-b]pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 16 steps

1.1: 97 percent / imidazole / dimethylformamide / 12 h / 20 °C

2.1: t-BuLi / tetrahydrofuran; pentane / 0.5 h / 0 °C

2.2: 95 percent / tetrahydrofuran; pentane / -70 - 20 °C

3.1: dimethyl dioxirane / CH₂Cl₂ / 0.5 h / -65 °C

3.2: 90 percent / CH₂Cl₂ / 0.25 h / -65 °C

4.1: 95 percent / NaH / hexamethylphosphoric acid triamide / 0.5 h / 0 °C

5.1: 86 percent / i-Pr₂NEt / CH₂Cl₂ / 3 h / -65 - 20 °C

6.1: 93 percent / DCC; DMAP / CH₂Cl₂ / 14 h / 20 °C

7.1: 100 percent / glacial AcOH / methanol; H₂O / 6 h / 0 °C

8.1: NaH / 4 h / 20 °C

8.2: 86 percent / 48 h / 20 °C

9.1: 19.4 mg / n-Bu₃SnH; AIBN / toluene / 2 h / 110 °C

10.1: 100 percent / TiCl₄; TMEDA; Zn / PbCl₂ / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

11.1: 77 percent / [N,N'-(Mes)2-imidazolidin-2-yl]Ru=CHPh(PCy₃)Cl₂ / benzene / 64 h / 80 °C

12.1: dimethyl dioxirane / CH₂Cl₂; acetone / -65 - 0 °C

13.1: 50 mg / DIBAL / CH₂Cl₂; toluene / 0.25 h / -65 °C

14.1: 100 percent / HF*pyridine / tetrahydrofuran / 3 h / 0 °C

15.1: 62 percent / 2,6-lutidine / CH₂Cl₂ / -65 - 20 °C

16.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; dmap; 2,2'-azobis(isobutyronitrile); N,N,N,N,-tetramethylethylenediamine; tert.-butyl lithium; tri-n-butyl-tin hydride; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; diisobutylaluminium hydride; pyridine hydrogenfluoride; acetic acid; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; pentane; benzene;
DOI:10.1021/ol034100w