(1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

Base Information

• Chemical Name: (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol
• CAS No.: 860267-66-9
• Molecular Formula: C₃₅H₅₂O₄
• Molecular Weight: 536.795
• Mol file: 860267-66-9.mol

Synonyms:(1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

Chemical Property of (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol

There total 12 articles about (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol 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:

(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane (860267-59-0) → (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol (860267-66-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

2.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

3.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

4.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

5.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

6.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

7.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

8.1: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

9.1: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

10.1: 2.53 g / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

11.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

11.2: 3.28 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; sodium periodate; n-butyllithium; samarium diiodide; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; diethylazodicarboxylate; methyl iodide; osmium(VIII) oxide; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 1.1: Lemieux-Johnson oxidation / 5.1: oxy-Michael addition / 9.1: Mitsunobu reaction / 11.2: Wittig reaction;

DOI:10.1021/ol0508126

Reference yield:

Trifluoro-methanesulfonic acid (4R,5R)-5-benzyloxymethyl-2,2-dimethyl-[1,3]dioxolan-4-ylmethyl ester (133842-56-5) → (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol (860267-66-9)

Guidance literature:

Multi-step reaction with 12 steps

1.1: CuBr / diethyl ether / 0.25 h / 0 °C

1.2: 11.2 g / diethyl ether / 2.5 h / 0 °C

2.1: 90 percent / NaIO₄ / OsO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 2.5 h / 20 °C

3.1: 74 percent / d-camphorsulfonic acid / methanol / 18 h / 0 °C

4.1: 96 percent / n-tetrabutylammonium iodide; sodium hydride / dimethylformamide / 2 h / 0 - 20 °C

5.1: 98 percent / zinc triflate / 1,2-dichloro-ethane / 6 h / 50 °C

6.1: 97 percent / N-methylmorpholine / CH₂Cl₂ / 14 h / 20 °C

7.1: 85 percent / iodomethane; NaHCO₃ / acetonitrile; H₂O / 28 h / 0 - 20 °C

8.1: 86 percent / samarium(II) iodide; methanol / tetrahydrofuran / 1 h / 0 °C

9.1: 1.31 g / aq. NaOH / ethanol / 2.5 h / 20 °C

10.1: 1.15 g / triphenylphosphine; diethyl azodicarboxylate / tetrahydrofuran; toluene / 2 h

11.1: 2.53 g / DIBAL / CH₂Cl₂; hexane / 1 h / -78 °C

12.1: n-BuLi / tetrahydrofuran; hexane / 1.5 h / -15 °C

12.2: 3.28 g / tetrahydrofuran; hexane / 18 h / -78 - 20 °C

With 4-methyl-morpholine; methanol; sodium hydroxide; sodium periodate; n-butyllithium; samarium diiodide; (1S)-10-camphorsulfonic acid; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; diisobutylaluminium hydride; sodium hydrogencarbonate; triphenylphosphine; copper(I) bromide; diethylazodicarboxylate; methyl iodide; osmium(VIII) oxide; In tetrahydrofuran; methanol; diethyl ether; ethanol; hexane; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene; acetonitrile; tert-butyl alcohol; 2.1: Lemieux-Johnson oxidation / 6.1: oxy-Michael addition / 10.1: Mitsunobu reaction / 12.2: Wittig reaction;

DOI:10.1021/ol0508126

Reference yield:

(3aR,5R,7aR)-5-((R)-1,2-Bis-benzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-ol + dodecyltriphenylphosphonium bromide (15510-55-1) → (1'R,2R,3R,6R)-6-(1',2'-bis-benzyloxy-ethyl)-2-tetradec-2-enyl-tetrahydro-pyran-3-ol (860267-66-9)

Guidance literature:

dodecyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -15 ℃; for 1.5h;

(3aR,5R,7aR)-5-((R)-1,2-Bis-benzyloxy-ethyl)-hexahydro-furo[3,2-b]pyran-2-ol; In tetrahydrofuran; hexane; at -78 - 20 ℃; for 18h;

DOI:10.1021/ol0508126

upstream raw materials:

dodecyltriphenylphosphonium bromide

(1R,2'R)-2-benzyloxy-1-(5'-methoxy-tetrahydrofuran-2'-yl)-ethanol

(4R,5R)-4-benzyloxymethyl-5-but-3-enyl-2,2-dimethyl-[1,3]dioxolane

(1'R,2R)-2-(1',2'-bis-benzyloxyethyl)-5-methoxy-tetrahydrofuran

Downstream raw materials:

(1'R,2R,3R,6R)-6-(1'-hydroxy-2'-p-toluenesulfonyloxy-ethyl)-3-methoxy-methoxy-2-tetradecyl-tetrahydropyran