(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal

Base Information

• Chemical Name: (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal
• CAS No.: 854749-23-8
• Molecular Formula: C₃₁H₄₀O₆
• Molecular Weight: 508.655
• Mol file: 854749-23-8.mol

Synonyms:(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal

Chemical Property of (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal

There total 14 articles about (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal 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: 84.0%

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enethioic acid S-ethyl ester (854931-23-0) → (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal (854749-23-8)

Guidance literature:

With diisobutylaluminium hydride; at -78 ℃;

DOI:10.1021/ol050511w

Reference yield:

(2R,3R)-2-((benzyloxy)methoxy)hex-5-en-3-ol → (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal (854749-23-8)

Guidance literature:

Multi-step reaction with 12 steps

1: KH / tetrahydrofuran

2: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

3: MgBr₂*Et₂O

4: 97 percent / imidazole / dimethylformamide

5: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

6: 92 percent / indium / dimethylformamide

7: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

8: O₃

9: 92 percent / NaH

10: HF*pyridine

11: camphorsulfonic acid / benzene / Heating

12: 84 percent / DIBAL-H / -78 °C

With 1H-imidazole; indium; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; camphor-10-sulfonic acid; hydrogen; sodium acetate; potassium hydride; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; ozone; pyridinium chlorochromate; magnesium bromide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 9: Horner-Emmons reaction;

DOI:10.1021/ol050511w

Reference yield:

1-[(R)-1-((R)-1-Benzyloxymethoxy-ethyl)-but-3-enyloxymethyl]-4-methoxy-benzene → (E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enal (854749-23-8)

Guidance literature:

Multi-step reaction with 11 steps

1: O₃; NaHCO₃ / CH₂Cl₂; methanol / -78 °C

2: MgBr₂*Et₂O

3: 97 percent / imidazole / dimethylformamide

4: 92 percent / Rh(acac)2(CO)2; triarylphosphite-based ligand; H₂

5: 92 percent / indium / dimethylformamide

6: 94 percent / PCC; molecular sieves 4 Angstroem; NaOAc / CH₂Cl₂

7: O₃

8: 92 percent / NaH

9: HF*pyridine

10: camphorsulfonic acid / benzene / Heating

11: 84 percent / DIBAL-H / -78 °C

With 1H-imidazole; indium; Rh(acac)2(CO)2; 4 A molecular sieve; triarylphosphite-based ligand; camphor-10-sulfonic acid; hydrogen; sodium acetate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; pyridine hydrogenfluoride; ozone; pyridinium chlorochromate; magnesium bromide; In methanol; dichloromethane; N,N-dimethyl-formamide; benzene; 8: Horner-Emmons reaction;

DOI:10.1021/ol050511w

upstream raw materials:

(E)-4-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-4-methyl-pent-2-enethioic acid S-ethyl ester

{1-[3-benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-but-3-enyloxy}-tert-butyl-dimethyl-silane

(5S,7R,8R)-8-Benzyloxymethoxy-5-(tert-butyl-dimethyl-silanyloxy)-7-(4-methoxy-benzyloxy)-nonanal

(7S,9R,10R)-10-Benzyloxymethoxy-7-(tert-butyl-dimethyl-silanyloxy)-9-(4-methoxy-benzyloxy)-2,2-dimethyl-3-oxo-undecanal

Downstream raw materials:

{2-[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-ethoxy}-tert-butyl-diphenyl-silane

[(2S,6R)-6-((E)-3-{(S)-6-[(2R,3R)-3-Benzyloxymethoxy-2-(4-methoxy-benzyloxy)-butyl]-5,6-dihydro-4H-pyran-2-yl}-3-methyl-but-1-enyl)-4-methylene-tetrahydro-pyran-2-yl]-acetaldehyde