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

Base Information

• Chemical Name: (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol
• CAS No.: 602301-72-4
• Molecular Formula: C₂₁H₃₄O₅Si
• Molecular Weight: 394.583
• Mol file: 602301-72-4.mol

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

Chemical Property of (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-1-ol

There total 3 articles about (E)-4-[(2R,4S,5R)-5-(tert-Butyl-dimethyl-silanyloxy)-2-(4-methoxy-phenyl)-[1,3]dioxan-4-yl]-but-2-en-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:

p-Anisaldehyde dimethyl acetal (2186-92-7) → (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)

Guidance literature:

Multi-step reaction with 3 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

With 1H-imidazole; diisobutylaluminium hydride; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide; 1.1: Wittig reaction;

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

Reference yield:

tert-butyldimethylsilyl chloride (18162-48-6) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

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

With 1H-imidazole; diisobutylaluminium hydride; In hexane; dichloromethane; N,N-dimethyl-formamide;

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) → (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)

Guidance literature:

Multi-step reaction with 2 steps

1: imidazole / dimethylformamide

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

With 1H-imidazole; diisobutylaluminium hydride; In hexane; dichloromethane; N,N-dimethyl-formamide;

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

upstream raw materials:

p-Anisaldehyde dimethyl acetal

tert-butyldimethylsilyl chloride

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

Downstream raw materials:

C₂₁H₃₄O₆Si

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

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

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