2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Name:2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester
CAS No.:130278-35-2
Molecular Formula:C₃₈H₅₆O₅Si
Molecular Weight:620.945
Hs Code.:

2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

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Chemical Property of 2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

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Technology Process of 2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

There total 25 articles about 2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl 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: 93.0%

: 130258-60-5,130258-89-8
(2R,3S,6R)-3-Methyl-2-<2-(trimethylacetoxy)ethyl>-6-<1-(trimethylsilyl)-2-propen-1-yl>tetrahydropyran

: 130258-61-6,130323-46-5,130324-85-5
(2R,S,5S)-5-<1(R)-<(tert-Butyldiphenylsilyl)oxy>-ethyl>-2-methoxytetrahydrofuran

: 130278-35-2,130324-84-4
2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at 0 ℃; for 1h;
DOI:10.1021/jo00036a026

Reference yield:

: 142459-13-0
(E)-(4R,5S)-4-Acetoxy-5-(methanesulfonyloxy)-2-hexenal

: 130278-35-2,130324-84-4
2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 98 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h

2: methanol / 9.5 h / 5 °C

3: imidazole / dimethylformamide / 1 h / Ambient temperature

4: 93 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; boron trifluoride diethyl etherate; hydrogen; palladium on activated charcoal; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jo00036a026

Reference yield:

: 119138-78-2,123151-77-9,123151-78-0,132077-95-3
(E)-4-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-but-2-enoic acid methyl ester

: 130278-35-2,130324-84-4
2,2-Dimethyl-propionic acid 2-[(2R,3S,6R)-6-((E)-3-{(S)-5-[(R)-1-(tert-butyl-diphenyl-silanyloxy)-ethyl]-tetrahydro-furan-2-yl}-propenyl)-3-methyl-tetrahydro-pyran-2-yl]-ethyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 97 percent / H₂ / 10percent Pd/C / ethyl acetate / 4 h / 760 Torr

2: 13.7 g / KOH / methanol; H₂O / 0.5 h / Ambient temperature

3: 20.3 g / DCC, DMAP / CH₂Cl₂ / 1) r.t., 1 d, 2) reflux, 2.5 h

4: 1) NaN(TMS)2 / 1) THF, -80 deg C, 1 h, 2) -80 deg C to -35 deg C, 1 h

5: 1) 30 percent H₂O₂, LiOH, H₂O 2) HCl / 1) THF, 30 min

6: 2.84 g / imidazole / CH₂Cl₂ / 1 h / Ambient temperature

7: 9.2 g / DIBALH / hexane; diethyl ether / 0.5 h

8: 10.5 g / acetonitrile / 18 h / Heating

9: 1) KOH 2) t-BuOK / 1) MeOH, r.t., 3.5 d 2) THF, r.t., 1.5 h

10: 88 percent / DIBALH / hexane; diethyl ether / 1 h / -70 - -20 °C

11: 98 percent / Et₃N, DMAP / CH₂Cl₂ / 2 h / Ambient temperature

12: 100 percent / TsOH, H₂O / acetone / 3 h

13: 1) oxalyl chloride, DMSO, 2) Et₃N / 1) CH₂Cl₂, -80 deg C to -40 deg C, 40 min, 2) -40 deg C to -10 deg C, 1 h

14: 76 percent / tetrahydrofuran; diethyl ether / 1.5 h / Ambient temperature

15: 76 percent / SOCl₂ / diethyl ether / 7 h / Ambient temperature

16: 96 percent / diethyl ether / -60 °C

17: 93 percent / BF₃*OEt₂ / CH₂Cl₂ / 1 h / 0 °C

With 1H-imidazole; hydrogenchloride; dmap; potassium hydroxide; lithium hydroxide; thionyl chloride; oxalyl dichloride; boron trifluoride diethyl etherate; potassium tert-butylate; water; hydrogen; dihydrogen peroxide; sodium hexamethyldisilazane; diisobutylaluminium hydride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; dicyclohexyl-carbodiimide; palladium on activated charcoal; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; ethyl acetate; acetone; acetonitrile;
DOI:10.1021/jo00036a026