C₂₁H₂₈O₃

Base Information

• Chemical Name: C₂₁H₂₈O₃
• CAS No.: 1271726-72-7
• Molecular Formula: C₂₁H₂₈O₃
• Molecular Weight: 328.452
• Mol file: 1271726-72-7.mol

Synonyms:C₂₁H₂₈O₃

Chemical Property of C₂₁H₂₈O₃

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of C₂₁H₂₈O₃

There total 8 articles about C₂₁H₂₈O₃ 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: 73.0%

(E)-4-((4S,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)but-2-enal (1271726-71-6) + allyltributylstanane (24850-33-7) → C21H28O3 (1271726-72-7)

Guidance literature:

(E)-4-((4S,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)but-2-enal; allyltributylstanane; With titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; silver(l) oxide; In dichloromethane; at 0 ℃; for 12h; Molecular sieve;

With trifluoroacetic acid; In tetrahydrofuran; at -78 - 20 ℃; for 4h; optical yield given as %ee; stereoselective reaction; Inert atmosphere;

DOI:10.1016/j.tetlet.2010.12.070

Reference yield:

(E)-3-phenylpropenal (14371-10-9) → C21H28O3 (1271726-72-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol / tetrahydrofuran / -78 - 20 °C / Molecular sieve; Inert atmosphere

1.2: -78 - 20 °C / Inert atmosphere

2.1: acetic acid; tetramethylammonium triacetoxyborohydride / acetonitrile / 5 h / -40 °C

3.1: camphor-10-sulfonic acid / dichloromethane / 2 h / 0 - 20 °C

4.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C

5.1: 2-iodoxybenzoic acid / dichloromethane; dimethyl sulfoxide / 4 h / 0 - 20 °C

6.1: dichloromethane / 3 h / 20 °C

7.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C

8.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; silver(l) oxide / dichloromethane / 12 h / 0 °C / Molecular sieve

8.2: 4 h / -78 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; 2-iodoxybenzoic acid; camphor-10-sulfonic acid; (R)-1,1'-Bi-2-naphthol; diisobutylaluminium hydride; acetic acid; silver(l) oxide; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; acetonitrile; 1.1: Mukaiyama reaction / 6.1: Wittig reaction / 8.1: Maruoka allylation;

DOI:10.1016/j.tetlet.2010.12.070

Reference yield:

C15H20O4 (70633-84-0) → C21H28O3 (1271726-72-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: camphor-10-sulfonic acid / dichloromethane / 2 h / 0 - 20 °C

2.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / 0 °C

3.1: 2-iodoxybenzoic acid / dichloromethane; dimethyl sulfoxide / 4 h / 0 - 20 °C

4.1: dichloromethane / 3 h / 20 °C

5.1: diisobutylaluminium hydride / tetrahydrofuran / 1 h / -78 °C

6.1: titanium(IV) isopropylate; (R)-1,1'-Bi-2-naphthol; silver(l) oxide / dichloromethane / 12 h / 0 °C / Molecular sieve

6.2: 4 h / -78 - 20 °C / Inert atmosphere

With titanium(IV) isopropylate; 2-iodoxybenzoic acid; camphor-10-sulfonic acid; (R)-1,1'-Bi-2-naphthol; diisobutylaluminium hydride; silver(l) oxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; 4.1: Wittig reaction / 6.1: Maruoka allylation;

DOI:10.1016/j.tetlet.2010.12.070

upstream raw materials:

(E)-3-phenylpropenal

C₁₅H₂₀O₄

ethyl 2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetate

2-((4R,6R)-2,2-dimethyl-6-((E)-styryl)-1,3-dioxan-4-yl)acetaldehyde

Downstream raw materials:

(6R)-5,6-dihydro-6-[(4'S*,6'R*,1'E,7'E)-4',6'-dihydroxy-8'-phenyl-1',7'-octadienyl]-2-pyrone

C₂₄H₃₀O₄