3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

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Chemical Name:3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol
CAS No.:602301-80-4
Molecular Formula:C₂₃H₃₈O₆Si
Molecular Weight:438.637
Hs Code.:

Synonyms:3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

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Chemical Property of 3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

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Technology Process of 3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

There total 13 articles about 3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-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: 77.0%

: 602301-79-1
[(2R,4aR,6S,7R,8aS)-6-Allyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

: 602301-80-4
3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

Guidance literature:: [(2R,4aR,6S,7R,8aS)-6-Allyl-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane; With dimeric 9-borabicyclo[3.3.1]nonane; In tetrahydrofuran; at 20 ℃; for 96h;

With sodium hydroxide; dihydrogen peroxide; at 20 ℃; for 30h;
DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 602301-80-4
3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 13 steps

1.1: tetrahydrofuran / Heating

1.2: 82 percent / CSA / CH₂Cl₂; tetrahydrofuran / 24 h / 20 °C

2.1: imidazole / dimethylformamide

3.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

5.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

6.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

7.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

8.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

9.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

10.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

10.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

11.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 3 h / 20 °C

12.1: t-BuOK / tetrahydrofuran / 1.5 h / 20 °C

13.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

13.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction / 4.1: Sharpless asymmetric epoxidation / 5.1: Swern oxidation / 6.1: Wittig reaction / 12.1: Wittig reaction;
DOI:10.1016/S0040-4020(03)00913-X

Reference yield:

: 602301-70-2
(E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate

: 602301-80-4
3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-propan-1-ol

Guidance literature:: Multi-step reaction with 12 steps

1.1: imidazole / dimethylformamide

2.1: DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

3.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

4.1: oxalyl chloride; DMSO; Et₃N / CH₂Cl₂ / 1 h / -78 °C

5.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

6.1: TBAF / tetrahydrofuran / 0.5 h / 20 °C

7.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

8.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

9.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

9.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

10.1: DMSO; Et₃N; SO₃*pyridine / CH₂Cl₂ / 3 h / 20 °C

11.1: t-BuOK / tetrahydrofuran / 1.5 h / 20 °C

12.1: 9-BBN dimer / tetrahydrofuran / 96 h / 20 °C

12.2: 77 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; titanium(IV) isopropylate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 3.1: Sharpless asymmetric epoxidation / 4.1: Swern oxidation / 5.1: Wittig reaction / 11.1: Wittig reaction;
DOI:10.1016/S0040-4020(03)00913-X