(4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol

Base Information

• Chemical Name: (4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol
• CAS No.: 1080425-38-2
• Molecular Formula: C₂₈H₅₂O₅Si₂
• Molecular Weight: 524.889
• Mol file: 1080425-38-2.mol

Synonyms:(4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol

Chemical Property of (4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol

There total 1 articles about (4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-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: 45.0%

(3R,4R)-4-tert-butyldimethylsilyloxy-3-(2-trimethylsilylethoxymethoxy)pentanal (884345-43-1) + [2-(bromomethyl)prop-2-en-1-yloxy]methylbenzene (347886-00-4) → (4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol (1080425-38-2) + (4S,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol (1080425-41-7)

Guidance literature:

With indium; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1055/s-2008-1078015

Reference yield: 92.0%

(4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol (1080425-38-2) + 4-nitro-benzoic acid (62-23-7) → C35H55NO8Si2

Guidance literature:

With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran;

DOI:10.1055/s-2008-1078015

Reference yield:

(4R,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol (1080425-38-2) → (2E)-(5S,7R,8R)-3-benzyloxymethyl-8-tertbutyldimethylsilyloxy-7-(2-trimethylsilylethoxymethoxy)non-2-ene-1,5-diol

Guidance literature:

Multi-step reaction with 5 steps

1: triphenylphosphine; di-isopropyl azodicarboxylate / tetrahydrofuran / 12 h / 0 - 20 °C

2: potassium carbonate / methanol / 3 h / 0 °C

3: N-ethyl-N,N-diisopropylamine / dichloromethane / 5 h / 0 °C

4: tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride / 1,2-dichloro-ethane / 2 h / Reflux

5: sodium tetrahydroborate; cerium(III) chloride heptahydrate / methanol / 2 h / 0 °C

With tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; sodium tetrahydroborate; cerium(III) chloride heptahydrate; di-isopropyl azodicarboxylate; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; 1,2-dichloro-ethane; 5: |Luche Cerium Reduction;

DOI:10.1039/c7ob02127e

upstream raw materials:

(3R,4R)-4-tert-butyldimethylsilyloxy-3-(2-trimethylsilylethoxymethoxy)pentanal

[2-(bromomethyl)prop-2-en-1-yloxy]methylbenzene

Downstream raw materials:

(4S,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-ol

(4S,6R,7R)-2-benzyloxymethyl-7-tertbutyldimethylsilyloxy-6-(2-trimethylsilylethoxymethoxy)oct-1-en-4-yl acrylate

(6S)-4-benzyloxymethyl-6-[(2R,3R)-3-tertbutyldimethylsilyloxy-2-(2-trimethylsilylethoxymethoxy)butyl]-5,6-dihydropyran-2-one

(2E)-(5S,7R,8R)-3-benzyloxymethyl-8-tert-butyldimethylsilyloxy-1-triisopropylsilyloxy-7-(2-trimethylsilylethoxymethoxy)non-2-en-5-ol