(R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane

Base Information

• Chemical Name: (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane
• CAS No.: 91527-01-4
• Molecular Formula: C₁₈H₂₆O₅
• Molecular Weight: 322.401
• Mol file: 91527-01-4.mol

Synonyms:(R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane

Chemical Property of (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane

There total 2 articles about (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane 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: 89.0%

(2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol (91603-58-6) + ethyl acetate (141-78-6) → (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane (91527-01-4)

Guidance literature:

titanium(IV) tetraethanolate; for 24h; Heating;

Reference yield: 70.7%

(2S,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol (91527-00-3) + acetic acid (64-19-7,77671-22-8) → (R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane (91527-01-4)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In toluene; benzene; at 23 ℃; for 16h;

DOI:10.1016/S0040-4039(01)80212-4

Reference yield:

(R,R,R)-5-acetoxy-1-benzyloxy-2,3-(isopropylidenedioxy)hexane (91527-01-4) → colletodiol (21142-67-6)

Guidance literature:

Multi-step reaction with 6 steps

1: 95 percent / hydrogen / Pd(OH)2/C (20percent,moist) / ethyl acetate / 0.05 h / 735.5 Torr / Ambient temperature

2: 1) oxalylchloride/DMSO, 2) TEA / 1) 15 min, -60 deg C, 2) CH₂Cl₂, r. t., 5 min

3: 68 g / dimethylformamide / 5 h / Ambient temperature

4: 99 percent / lithium hydroxide / tetrahydrofuran; H₂O / 2 h / Ambient temperature

5: 1) 2,4,6-trichlorobenzoyl chloride, trimethylamine, 2) 4-(dimethylamino)pyridine / 1) THF, room temp., 2 h, 2) toluene, room temp., 4.5 h

6: 90 percent / 1.5 M bromodimethylborane, 1,2-dichloroethane / CH₂Cl₂ / 1 h / -78 °C

With dmap; lithium hydroxide; dimethylboron bromide; Chloro-oxo-acetic acid; TEA; 2,4,6-trichlorobenzoyl chloride; hydrogen; dimethyl sulfoxide; 1,2-dichloro-ethane; trimethylamine; palladium hydroxide - carbon; In tetrahydrofuran; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide;

upstream raw materials:

(2S,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol

acetic acid

(2R,4R,5R)-6-benzyloxy-4,5-isopropylidenedioxy-2-hexanol

ethyl acetate

Downstream raw materials:

colletodiol

E-(4R,5R,7R)-trihydroxy-2-octenoic acid