(1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane

Base Information

• Chemical Name: (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane
• CAS No.: 121693-62-7
• Molecular Formula: C₁₈H₂₆O₄
• Molecular Weight: 306.402
• Mol file: 121693-62-7.mol

Synonyms:(1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane

Chemical Property of (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane

There total 4 articles about (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane 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: 79.0%

2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol (121693-61-6) + ethyl chloromethyl ether (3188-13-4) → (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane (121693-62-7)

Guidance literature:

With sodium hydride; In dichloromethane; 1.) 0 deg C, 10 min., 2.) 23 deg C, 24 h., 3.) 55 deg C, 48 h.;

DOI:10.1016/0040-4039(88)85113-X

Reference yield:

Geraniol (106-24-1) → (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane (121693-62-7)

Guidance literature:

Multi-step reaction with 5 steps

1: Ti(OiPr)4, t-BuOOH, (-)-diethyl (2R,3R)-tartrate / in the presence of molecular sieves

2: 82 percent / NaH / tetrahydrofuran / 14 h / 23 °C

3: 85 percent / 0.18 M perchloric acid / tetrahydrofuran; H₂O / 14 h / 23 °C

4: 43 percent / 1.05 eq. powdered pyridium chlorochromate / CH₂Cl₂ / 10 h / 23 °C

5: 79 percent / sodium hydride / CH₂Cl₂ / 1.) 0 deg C, 10 min., 2.) 23 deg C, 24 h., 3.) 55 deg C, 48 h.

With titanium(IV) isopropylate; tert.-butylhydroperoxide; perchloric acid; diethyl (2R,3R)-tartrate; sodium hydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/0040-4039(88)85113-X

Reference yield:

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol (50727-94-1,62777-72-4,62960-04-7,71030-55-2,76985-26-7,82188-73-6,112456-40-3,112456-65-2,62777-71-3) → (1S,2R,7R)-2-Benzyloxymethyl-1,6,6-trimethyl-3,5,10-trioxa-bicyclo[5.2.1]decane (121693-62-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / NaH / tetrahydrofuran / 14 h / 23 °C

2: 85 percent / 0.18 M perchloric acid / tetrahydrofuran; H₂O / 14 h / 23 °C

3: 43 percent / 1.05 eq. powdered pyridium chlorochromate / CH₂Cl₂ / 10 h / 23 °C

4: 79 percent / sodium hydride / CH₂Cl₂ / 1.) 0 deg C, 10 min., 2.) 23 deg C, 24 h., 3.) 55 deg C, 48 h.

With perchloric acid; sodium hydride; In tetrahydrofuran; dichloromethane; water;

DOI:10.1016/0040-4039(88)85113-X

upstream raw materials:

2-[(2R,5S)-5-((R)-2-Benzyloxy-1-hydroxy-ethyl)-5-methyl-tetrahydro-furan-2-yl]-propan-2-ol

ethyl chloromethyl ether

Geraniol

(2R,3R)-3-methyl-3-(4-methyl-3-pentenyl)oxiranemethanol

Downstream raw materials:

venustatriol