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

Base Information

Chemical Name:[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde
CAS No.:918897-16-2
Molecular Formula:C₂₂H₃₄O₆Si
Molecular Weight:422.594
Hs Code.:

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

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

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

There total 11 articles about [(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde 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: 100.0%

: 602301-78-0
2-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-ethanol

: 918897-16-2
[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

Guidance literature:: With Dess-Martin periodane; In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmcl.2006.09.004

Reference yield:

: 2186-92-7
p-Anisaldehyde dimethyl acetal

: 918897-16-2
[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 11 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

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; 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;
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

: 918897-16-2
[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-acetaldehyde

Guidance literature:: Multi-step reaction with 10 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

With 1H-imidazole; tert.-butylhydroperoxide; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; 4 A molecular sieve; 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;
DOI:10.1016/S0040-4020(03)00913-X