(3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate

Base Information

• Chemical Name: (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate
• CAS No.: 73454-55-4
• Molecular Formula: C₂₃H₃₇O₅P
• Molecular Weight: 424.518
• Mol file: 73454-55-4.mol

Synonyms:

Chemical Property of (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate

There total 9 articles about (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate 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:

Nerol (106-25-2) → (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate (73454-55-4)

Guidance literature:

Multi-step reaction with 8 steps

1: NaH / DME 1) 80-85 deg C/ 1.5 h 2a) 1h reflux 2b) 16 h at r.t.

2: 1) O₃ / pyridine 2) Me₂S / 1) CH₂Cl₂ / -78 deg C 2) r.t./overnight

3: 87 percent / NaBH₄ / ethanol / 3.5 h / Ambient temperature

4: 93 percent / pyridine / 24 h / 0 °C

5: 92 percent / LiBr / acetone / 21.5 h / Heating

6: 1) Mg / Br(CH₂)2Br / 1) ether / 1h / reflux 2) 1h reflux, then 18.5h at r.t.

7: 72 percent / CrO₃ (Collins reagent) / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

8: 1) LDA / 1) THF / HMPA / 40 min / r.t. 2) 19h / r.t.

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; dimethylsulfide; sodium hydride; ozone; magnesium; ethylene dibromide; lithium bromide; lithium diisopropyl amide; In pyridine; ethanol; dichloromethane; acetone;

DOI:10.1021/jo01301a028

Reference yield:

(Z)-6-(benzyloxy)-4-methylhex-4-enal (55802-99-8) → (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate (73454-55-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 87 percent / NaBH₄ / ethanol / 3.5 h / Ambient temperature

2: 93 percent / pyridine / 24 h / 0 °C

3: 92 percent / LiBr / acetone / 21.5 h / Heating

4: 1) Mg / Br(CH₂)2Br / 1) ether / 1h / reflux 2) 1h reflux, then 18.5h at r.t.

5: 72 percent / CrO₃ (Collins reagent) / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

6: 1) LDA / 1) THF / HMPA / 40 min / r.t. 2) 19h / r.t.

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; magnesium; ethylene dibromide; lithium bromide; lithium diisopropyl amide; In pyridine; ethanol; dichloromethane; acetone;

DOI:10.1021/jo01301a028

Reference yield:

(2Z)-1-(benzyloxy)-3,7-dimethylocta-2,6-diene (55802-98-7) → (3Z,7Z)-9-benzyloxy-2,2,7-trimethyl-3,7-nonadien-3-yl diethyl phosphate (73454-55-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) O₃ / pyridine 2) Me₂S / 1) CH₂Cl₂ / -78 deg C 2) r.t./overnight

2: 87 percent / NaBH₄ / ethanol / 3.5 h / Ambient temperature

3: 93 percent / pyridine / 24 h / 0 °C

4: 92 percent / LiBr / acetone / 21.5 h / Heating

5: 1) Mg / Br(CH₂)2Br / 1) ether / 1h / reflux 2) 1h reflux, then 18.5h at r.t.

6: 72 percent / CrO₃ (Collins reagent) / pyridine / CH₂Cl₂ / 8 h / Ambient temperature

7: 1) LDA / 1) THF / HMPA / 40 min / r.t. 2) 19h / r.t.

With pyridine; chromium(VI) oxide; sodium tetrahydroborate; dimethylsulfide; ozone; magnesium; ethylene dibromide; lithium bromide; lithium diisopropyl amide; In pyridine; ethanol; dichloromethane; acetone;

DOI:10.1021/jo01301a028

upstream raw materials:

(Z)-9-benzyloxy-2,2,7-trimethyl-7-nonen-3-one

diethyl chlorophosphate

Nerol

(Z)-6-(benzyloxy)-4-methylhex-4-enal