(2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene

Base Information

• Chemical Name: (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene
• CAS No.: 915149-80-3
• Molecular Formula: C₂₁H₂₂O₂
• Molecular Weight: 306.404
• Mol file: 915149-80-3.mol

Synonyms:(2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene

Chemical Property of (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene

There total 6 articles about (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene 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: 94.0%

(2R,3R)-2,2-diallyl-4,5-dibenzyl-[1,3]dioxolane (915149-78-9) → (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene (915149-80-3)

Guidance literature:

tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; at 40 ℃; for 5h;

DOI:10.1021/ol062020x

Reference yield:

allylbenzene (300-57-2,57807-91-7) → (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene (915149-80-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 89 percent / Grubbs' first-generation catalyst / CH₂Cl₂ / 18 h / 40 °C

2: 89 percent / potassium ferricyanide; potassium carbonate; AD-mix-β / osmium tetroxide; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 48 h / 18 °C

3: 72 percent / p-toluenesulfonic acid / benzene / 18 h / 80 °C

4: 94 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 5 h / 40 °C

With AD-mix-β; potassium carbonate; toluene-4-sulfonic acid; potassium hexacyanoferrate(III); tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; osmium(VIII) oxide; Grubbs catalyst first generation; methanesulfonamide; In dichloromethane; water; tert-butyl alcohol; benzene;

DOI:10.1021/ol062020x

Reference yield:

1, 6-heptadien-4-ol (2883-45-6) → (2R,3R)-2,3-dibenzyl-1,4-dioxaspiro[4.4]non-7-ene (915149-80-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / pyridinium chlorochromate / CH₂Cl₂ / 72 h / 18 °C

2: 72 percent / p-toluenesulfonic acid / benzene / 18 h / 80 °C

3: 94 percent / Grubbs' second-generation catalyst / CH₂Cl₂ / 5 h / 40 °C

With toluene-4-sulfonic acid; pyridinium chlorochromate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In dichloromethane; benzene;

DOI:10.1021/ol062020x

upstream raw materials:

(2R,3R)-2,2-diallyl-4,5-dibenzyl-[1,3]dioxolane

allylbenzene

1, 6-heptadien-4-ol

vinylmethyl ketone

Downstream raw materials:

6,6-dibromobicyclo[3.1.0]hexan-3-one (2R,3R)-2,3-dibenzylethylene ketal

(2'R,3'R,7'R)-3-{8'-bromo-2,3-dibenzyl-1',4'-dioxaspiro[4.5]dec-8'-en-7'-yl}indole

(2'R,3'R,7'S)-3-{8'-bromo-2',3'-dibenzyl-1',4'-dioxaspiro[4.5]dec-8'-en-7'-yl}indole

Refernces