(R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol

Base Information

• Chemical Name: (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol
• CAS No.: 96944-15-9
• Molecular Formula: C₂₆H₄₂O₃
• Molecular Weight: 402.618
• Mol file: 96944-15-9.mol

Synonyms:(R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol

Chemical Property of (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol

There total 11 articles about (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-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: 80.0%

Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester (96944-16-0) → (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol (96944-15-9)

Guidance literature:

With KO₂; In dimethyl sulfoxide; Ambient temperature;

DOI:10.1016/S0040-4039(00)94886-X

Reference yield:

(6S,7S)-Dodeca-3,9-diyne-6,7-diol (96964-07-7) → (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol (96944-15-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 72 percent / p-TsOH / benzene / Heating

2: H₂ / 5percent Pd-Pb/CaCO₃ / hexane / Ambient temperature

3: 91 percent / Diisobutylaluminium hydride / CH₂Cl₂ / Ambient temperature

4: 89 percent / CH₂Cl₂ / -78 °C

5: 2,4,6-triisopropylbenzenesulfonyl hydrazide / tetrahydrofuran / Heating

6: 80 percent / 30percent H₂O₂ / tetrahydrofuran / Ambient temperature

7: 1.) 10 molpercent OsO₄, NMO, 2.) Pb(OAc)4 / 1.) aq. acetone, room temp., 2.) THF, -30 deg C,

8: diethyl ether / -78 °C

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; trisylhydrazine; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1016/S0040-4039(00)94886-X

Reference yield:

(4S,5S)-4,5-Di-pent-2-ynyl-2-phenyl-[1,3]dioxolane (96960-97-3) → (R)-1-((2R,4S,5S)-4-Benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-en-1-ol (96944-15-9)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / 5percent Pd-Pb/CaCO₃ / hexane / Ambient temperature

2: 91 percent / Diisobutylaluminium hydride / CH₂Cl₂ / Ambient temperature

3: 89 percent / CH₂Cl₂ / -78 °C

4: 2,4,6-triisopropylbenzenesulfonyl hydrazide / tetrahydrofuran / Heating

5: 80 percent / 30percent H₂O₂ / tetrahydrofuran / Ambient temperature

6: 1.) 10 molpercent OsO₄, NMO, 2.) Pb(OAc)4 / 1.) aq. acetone, room temp., 2.) THF, -30 deg C,

7: diethyl ether / -78 °C

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; trisylhydrazine; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; Lindlar's catalyst; palladium-lead; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4039(00)94886-X

upstream raw materials:

(2R,4S,5S)-tetrahydro-4-hydroxy-5-pentyl-2-furfuraldehyde (benzylate)

non-8-en-1-ylmagnesium bromide

Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester

(6S,7S)-Dodeca-3,9-diyne-6,7-diol