(E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene

Base Information

• Chemical Name: (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene
• CAS No.: 154814-99-0
• Molecular Formula: C₂₁H₂₄O₄S
• Molecular Weight: 372.485
• Mol file: 154814-99-0.mol

Synonyms:(E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene

Chemical Property of (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene

There total 3 articles about (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene 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: 95.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-(3R)-3-(benzyloxy)-4,6-heptadienol (154815-14-2) → (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene (154814-99-0)

Guidance literature:

With pyridine; 1.) 0 deg C, 2 h, 2.) r.t., 2 h;

DOI:10.1021/jo00085a026

Reference yield:

(2R,4R)-4-formyl-2-phenyl-1,3-dioxane (102794-92-3,145958-02-7,134665-69-3) → (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene (154814-99-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 49 percent / t-BuOK / tetrahydrofuran / 1.) r.t., 20 min, 2.) r.t., 5 min

2: 1.) DIBALH, 2.) I₂ / 1.) CH₂Cl₂, hexane, r.t., 1.5 h, 2.) benzene, irradiation, 30 min

3: 95 percent / pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 2 h

With pyridine; potassium tert-butylate; iodine; diisobutylaluminium hydride; In tetrahydrofuran;

DOI:10.1021/jo00085a026

Reference yield:

(2R,4R)-4-(1,3-butadienyl)-2-phenyl-1,3-dioxane → (E)-(R)-3-(benzyloxy)-1-<(p-tolylsulfonyl)oxy>-4,6-heptadiene (154814-99-0)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) DIBALH, 2.) I₂ / 1.) CH₂Cl₂, hexane, r.t., 1.5 h, 2.) benzene, irradiation, 30 min

2: 95 percent / pyridine / 1.) 0 deg C, 2 h, 2.) r.t., 2 h

With pyridine; iodine; diisobutylaluminium hydride;

DOI:10.1021/jo00085a026

upstream raw materials:

p-toluenesulfonyl chloride

(E)-(3R)-3-(benzyloxy)-4,6-heptadienol

(2R,4R)-4-formyl-2-phenyl-1,3-dioxane

Downstream raw materials:

(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-dihydroxypropyl>piperidin-6-one

(4aS,5R)-5-(benzyloxy)-2,4a,5,6,7,8-hexahydropyrido<1,2-b><1,2>oxazin-8-one

(2R,3R)-3-(benzyloxy)-2-<(1S,2R)-3-(tert-butyldiphenylsilyloxy)-1,2-(isopropylidenedioxy)propyl>piperidin-6-one

(2R,3R)-3-(benzyloxy)-2-<(Z)-3-(tert-butyldiphenylsilyloxy)-1-propenyl>piperidin-6-one