tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

Base Information

Chemical Name:tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane
CAS No.:289666-99-5
Molecular Formula:C₂₈H₃₈O₅Si
Molecular Weight:482.692
Hs Code.:

Synonyms:tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

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Chemical Property of tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

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Technology Process of tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

There total 14 articles about tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane 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: 83.0%

: 289667-03-4
(+)-(2R,3R,4R,5S)-1-tert-butyldiphenylsilyloxy-6,6-dimethyl-3-hydroxy-5-methoxy-2,4-methylenedioxyoct-7-en-3-ol

: 289666-99-5
tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

Guidance literature:: With oxygen; copper(l) chloride; palladium dichloride; In water; N,N-dimethyl-formamide;
DOI:10.1021/ol000072v

Reference yield:

: 108341-87-3
(2R,3R)-3-O-benzyl-1,2-O-isopropylidene-4-pentene-1,2,3-triol

: 289666-99-5
tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

Guidance literature:: Multi-step reaction with 14 steps

1.1: OsO₄; NMO

2.1: DMAP; Et₃N

3.1: 98 percent / AcOH; H₂O / tetrahydrofuran / 55 °C

4.1: 89 percent / pyridine

5.1: 88 percent / P₂O₅

6.1: 99 percent / DIBALH / 0 °C

7.1: (COCl)2; DMSO; Et₃N / -78 - -40 °C

8.1: TiCl₄ / CH₂Cl₂ / -78 °C

9.1: 95 percent / NaH / 0 - 20 °C

10.1: 100 percent / DIBALH / 0 °C

11.1: 97 percent / SO₃*Py; DMSO; Et₃N

12.1: 100 percent / BuLi / 0 - 20 °C

13.1: liq. NH₃; Li / -78 °C

13.2: 74 percent / DDQ

14.1: 83 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O

With pyridine; dmap; osmium(VIII) oxide; n-butyllithium; N-methyl-2-indolinone; oxalyl dichloride; pyridine-SO₃ complex; ammonia; water; oxygen; phosphorus pentoxide; titanium tetrachloride; lithium; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: hydroxylation / 2.1: silylation / 3.1: Hydrolysis / 4.1: Esterification / 5.1: cyclocondensation / 6.1: Reduction / 7.1: Swern oxidation / 8.1: Condensation / 9.1: Methylation / 10.1: Reduction / 11.1: Oxidation / 12.1: Wittig reaction / 13.1: Reduction / 13.2: Oxidation / 14.1: Cyclization;
DOI:10.1021/ol000072v

Reference yield:

: (2RS,3R,4R)-3-benzyloxy-4,5-isopropylidenedioxy-1,2-pentanediol

: 289666-99-5
tert-Butyl-((4R,4aR,8S,8aR)-8-methoxy-7,7-dimethyl-6-methylene-hexahydro-pyrano[3,2-d][1,3]dioxin-4-ylmethoxy)-diphenyl-silane

Guidance literature:: Multi-step reaction with 13 steps

1.1: DMAP; Et₃N

2.1: 98 percent / AcOH; H₂O / tetrahydrofuran / 55 °C

3.1: 89 percent / pyridine

4.1: 88 percent / P₂O₅

5.1: 99 percent / DIBALH / 0 °C

6.1: (COCl)2; DMSO; Et₃N / -78 - -40 °C

7.1: TiCl₄ / CH₂Cl₂ / -78 °C

8.1: 95 percent / NaH / 0 - 20 °C

9.1: 100 percent / DIBALH / 0 °C

10.1: 97 percent / SO₃*Py; DMSO; Et₃N

11.1: 100 percent / BuLi / 0 - 20 °C

12.1: liq. NH₃; Li / -78 °C

12.2: 74 percent / DDQ

13.1: 83 percent / PdCl₂; CuCl; O₂ / dimethylformamide; H₂O

With pyridine; dmap; n-butyllithium; oxalyl dichloride; pyridine-SO₃ complex; ammonia; water; oxygen; phosphorus pentoxide; titanium tetrachloride; lithium; sodium hydride; diisobutylaluminium hydride; acetic acid; dimethyl sulfoxide; triethylamine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: silylation / 2.1: Hydrolysis / 3.1: Esterification / 4.1: cyclocondensation / 5.1: Reduction / 6.1: Swern oxidation / 7.1: Condensation / 8.1: Methylation / 9.1: Reduction / 10.1: Oxidation / 11.1: Wittig reaction / 12.1: Reduction / 12.2: Oxidation / 13.1: Cyclization;
DOI:10.1021/ol000072v