[(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

Base Information

• Chemical Name: [(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
• CAS No.: 602301-79-1
• Molecular Formula: C₂₃H₃₆O₅Si
• Molecular Weight: 420.621

Synonyms:[(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

Chemical Property of [(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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(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

There total 12 articles about [(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 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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → [(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 (602301-79-1)

Guidance literature:

Multi-step reaction with 12 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

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:

(E)-ethyl 4-((2R,4S,5R)-5-hydroxy-2-(4-methoxyphenyl)-1,3-dioxan-4-yl)but-2-enoate (602301-70-2) → [(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 (602301-79-1)

Guidance literature:

Multi-step reaction with 11 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

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

Reference yield:

(E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol (602301-72-4) → [(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 (602301-79-1)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 139.35 g / diethyl-D-tartrate; molecular sieves 4 Angstroem; t-butylhydroperoxide / titanium(IV) tetraisopropoxide / CH₂Cl₂ / 27 h / -30 °C

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

3.1: 30 g / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.33 h / 0 °C

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

5.1: 15.8 g / PPTS / CH₂Cl₂ / 3 h / 0 °C

6.1: 98 percent / imidazole / dimethylformamide / 1.5 h / 20 °C

7.1: 9-BBN dimer / tetrahydrofuran / 38 h / 20 °C

7.2: 83 percent / 10 percent NaOH; 30 percent H₂O₂ / 30 h / 20 °C

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

9.1: t-BuOK / tetrahydrofuran / 1.5 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; dimethyl sulfoxide; triethylamine; dimeric 9-borabicyclo[3.3.1]nonane; titanium(IV) isopropylate; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 1.1: Sharpless asymmetric epoxidation / 2.1: Swern oxidation / 3.1: Wittig reaction / 9.1: Wittig reaction;

DOI:10.1016/S0040-4020(03)00913-X

upstream raw materials:

Methyltriphenylphosphonium bromide

[(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

p-Anisaldehyde dimethyl acetal

(2R,4aR,6S,7R,8aS)-2-(4-Methoxy-phenyl)-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

Downstream raw materials:

tert-Butyl-[(2R,4aR,6S,7R,8aS)-2-(4-methoxy-phenyl)-6-(3-phenylsulfanyl-propyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

[(2R,4aR,6S,7R,8aS)-6-{3-[(2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-(1-ethoxy-ethoxymethyl)-tetrahydro-pyran-3-yloxy]-3-phenylsulfanyl-propyl}-2-(4-methoxy-phenyl)-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-tert-butyl-dimethyl-silane

(2R,4aR,5aS,8R,9S,10aR,11aS)-8-((2R,3S,5R,6S)-5-Benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-9-vinyl-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

(2R,4aR,5aS,8R,9S,10aR,11aS)-9-Allyl-8-((2R,3S,5R,6S)-5-benzyloxy-6-benzyloxymethyl-2-vinyl-tetrahydro-pyran-3-yloxy)-2-(4-methoxy-phenyl)-decahydro-1,3,5,10-tetraoxa-cyclohepta[b]naphthalene

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