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

Base Information

• Chemical Name: Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester
• CAS No.: 96944-16-0
• Molecular Formula: C₂₇H₄₄O₅S
• Molecular Weight: 480.709

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

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

Chemical Property:

Purity/Quality:

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

There total 8 articles about Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester 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:

(6S,7S)-Dodeca-3,9-diyne-6,7-diol (96964-07-7) → Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester (96944-16-0)

Guidance literature:

Multi-step reaction with 9 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

9: Et₃N / CH₂Cl₂ / Ambient temperature

With lead(IV) acetate; osmium(VIII) oxide; N-methyl-2-indolinone; trisylhydrazine; hydrogen; dihydrogen peroxide; diisobutylaluminium hydride; toluene-4-sulfonic acid; triethylamine; 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) → Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester (96944-16-0)

Guidance literature:

Multi-step reaction with 8 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

8: Et₃N / CH₂Cl₂ / Ambient temperature

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

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

Reference yield:

(2R,4S,5S)-tetrahydro-4-hydroxy-5-pentyl-2-furfuraldehyde (benzylate) (96944-13-7) → Methanesulfonic acid (S)-1-((2R,4S,5S)-4-benzyloxy-5-pentyl-tetrahydro-furan-2-yl)-dec-9-enyl ester (96944-16-0)

Guidance literature:

Multi-step reaction with 2 steps

1: diethyl ether / -78 °C

2: Et₃N / CH₂Cl₂ / Ambient temperature

With triethylamine; In diethyl ether; dichloromethane;

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

upstream raw materials:

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

methanesulfonyl chloride

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

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

Downstream raw materials:

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

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