(4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane

Base Information

• Chemical Name: (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane
• CAS No.: 101906-28-9
• Molecular Formula: C₂₂H₃₄O₄
• Molecular Weight: 362.51
• Mol file: 101906-28-9.mol

Synonyms:(4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane

Chemical Property of (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane

There total 12 articles about (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane 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: 90.0%

4-Nitro-benzoic acid (E)-(1S,6R)-7-benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4,6-dimethyl-hept-3-enyl ester (114125-39-2) → (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane (101906-28-9)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1039/P19870002189

Reference yield:

(S)-(+)-3-benzyloxy-2-methylpropyl bromide (63930-50-7) → (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane (101906-28-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 51 percent / ethylenediamine / dimethylsulfoxide / 1.) 8 deg C; 2.) 20 min, r.t.

With ethylenediamine; In dimethyl sulfoxide;

DOI:10.1039/P19870002189

Reference yield:

(2R,S)-((2S)-3-benzyloxy-2-methylpropoxy)tetrahydropyran (104265-23-8) → (4S)-4-<(2R,7R)-(4E)-8-benzyloxy-2-hydroxy-5,7-dimethyloct-4-en-1-yl>-2,2-dimethyl-1,3-dioxolane (101906-28-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / Amberlite 120 ion exchange resin / methanol / 16 h / Ambient temperature

2: 86 percent / N-bromosuccinimide, PPh₃ / CH₂Cl₂ / 1.) 10-18 deg C; 2.) 45 min, r.t.

3: 51 percent / ethylenediamine / dimethylsulfoxide / 1.) 8 deg C; 2.) 20 min, r.t.

With N-Bromosuccinimide; Amberlite 120 ion exchange resin; ethylenediamine; triphenylphosphine; In methanol; dichloromethane; dimethyl sulfoxide;

DOI:10.1039/P19870002189

upstream raw materials:

trimethylaluminum

(2R)-benzyl-(2-methylpent-4-ynyl) ether

(S)-2,2-dimethyl-4-((S)-oxiran-2-ylmethyl)-1,3-dioxolane

4-Nitro-benzoic acid (E)-(1S,6R)-7-benzyloxy-1-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl)-4,6-dimethyl-hept-3-enyl ester

Downstream raw materials:

(E)-(2S,4R,9R)-10-Benzyloxy-4-(tert-butyl-dimethyl-silanyloxy)-1-((5S,6R)-5,6-dimethyl-5,6-dihydro-4H-pyran-2-yl)-7,9-dimethyl-dec-6-en-2-ol

(2S,4R,9R)-(6E)-1,2-epoxy-10-benzyloxy-7,9-dimethyl-4-(dimethyl-t-butylsilyloxy)dec-6-ene

(2S,4R,9R)-(6E)-10-benzyloxy-1,2-epoxy-7,9-dimethyldec-6-ene-4-ol

(2S,4S,6S,8R,9S)-2-<(5R)-(2E)-6-Benzyloxy-3,5-dimethyl-2-hexen-1-yl>-8,9-dimethyl-4-hydroxy-1,7-dioxaspiro<5.5>undecane