3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

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Chemical Name:3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one
CAS No.:912295-25-1
Molecular Formula:C₅₁H₇₀O₇
Molecular Weight:795.113
Hs Code.:

Synonyms:3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

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Chemical Property of 3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

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Technology Process of 3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

There total 17 articles about 3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one 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: 65.0%

: 912295-24-0
5'-(1-benzyloxydeca-2,9-diynyl)-5-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl

: 438037-20-8
(5S)-5-methyl-3-[(2S)-oxiran-2-ylmethyl]furan-2(5H)-one

: 912295-25-1
3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

Guidance literature:: 5'-(1-benzyloxydeca-2,9-diynyl)-5-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 0.5h;

(5S)-5-methyl-3-[(2S)-oxiran-2-ylmethyl]furan-2(5H)-one; With boron trifluoride diethyl etherate; In tetrahydrofuran; for 3h;
DOI:10.1021/ol061847o

Reference yield:

: 912295-20-6
acetic acid 1-but-3-enyl-2-hydroxyhex-5-enyl ester

: 912295-25-1
3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 82 percent / tert-butylhydroperoxide; O₂; Co(II)(modp)2 / propan-2-ol; H₂O; 2,2,4-trimethyl-pentane / 50 °C / 760 Torr

2.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C

3.1: 99 percent / EtMgBr / diethyl ether / 1 h / 0 °C

4.1: 79 percent / tert-butylhydroperoxide; O₂; Co(II) (modp)2 / propan-2-ol; H₂O; 2,2,4-trimethyl-pentane / 50 °C / 760 Torr

5.1: 96 percent / dimethylsulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

6.1: n-BuLi; TiCl(O-i-Pr)3 / diethyl ether; hexane; toluene / 0.5 h / cooling

6.2: diethyl ether; hexane; toluene / 8 h / 0 °C

7.1: 85 percent / H₂ / palladium on carbon / benzene / 8 h / 760 Torr

8.1: 92 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 0 °C

9.1: 98 percent / HCl / methanol / 2 h / 20 °C

10.1: 97 percent / dimethylsulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

11.1: Zn(OTf)2; (1R,2S)-(-)-N-methylephedrine; Et₃N / toluene / 1 h / 50 °C

11.2: toluene / 48 h

12.1: 74 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 0 °C

13.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

13.2: 65 percent / BF₃*Et₂O / tetrahydrofuran / 3 h

With 1H-imidazole; triisopropoxytitanium(IV) chloride; hydrogenchloride; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; Co(II) (modp)2; Co(II)(modp)2; (-)-N-methylephedrine; ethylmagnesium bromide; hydrogen; oxygen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; benzene; 5.1: Swern oxidation / 10.1: Swern oxidation;
DOI:10.1021/ol061847o

Reference yield:

: 912295-21-7
acetic acid 1-(5-hydroxymethyltetrahydrofuran-2-yl)-pent-4-enyl ester

: 912295-25-1
3-{13-benzyloxy-13-[5'-(1-benzyloxyundecyl)octahydro-[2,2']bifuranyl-5-yl]-2-hydroxytrideca-4,11-diynyl}-5-methyl-5H-furan-2-one

Guidance literature:: Multi-step reaction with 12 steps

1.1: 94 percent / imidazole / dimethylformamide / 16 h / 20 °C

2.1: 99 percent / EtMgBr / diethyl ether / 1 h / 0 °C

3.1: 79 percent / tert-butylhydroperoxide; O₂; Co(II) (modp)2 / propan-2-ol; H₂O; 2,2,4-trimethyl-pentane / 50 °C / 760 Torr

4.1: 96 percent / dimethylsulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

5.1: n-BuLi; TiCl(O-i-Pr)3 / diethyl ether; hexane; toluene / 0.5 h / cooling

5.2: diethyl ether; hexane; toluene / 8 h / 0 °C

6.1: 85 percent / H₂ / palladium on carbon / benzene / 8 h / 760 Torr

7.1: 92 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 0 °C

8.1: 98 percent / HCl / methanol / 2 h / 20 °C

9.1: 97 percent / dimethylsulfoxide; oxalyl chloride; Et₃N / CH₂Cl₂ / -78 - 20 °C

10.1: Zn(OTf)2; (1R,2S)-(-)-N-methylephedrine; Et₃N / toluene / 1 h / 50 °C

10.2: toluene / 48 h

11.1: 74 percent / NaH; Bu₄NI / dimethylformamide / 16 h / 0 °C

12.1: n-BuLi / tetrahydrofuran / 0.5 h / -78 °C

12.2: 65 percent / BF₃*Et₂O / tetrahydrofuran / 3 h

With 1H-imidazole; triisopropoxytitanium(IV) chloride; hydrogenchloride; tert.-butylhydroperoxide; n-butyllithium; oxalyl dichloride; Co(II) (modp)2; (-)-N-methylephedrine; ethylmagnesium bromide; hydrogen; oxygen; tetra-(n-butyl)ammonium iodide; zinc trifluoromethanesulfonate; sodium hydride; dimethyl sulfoxide; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; diethyl ether; hexane; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol; toluene; benzene; 4.1: Swern oxidation / 9.1: Swern oxidation;
DOI:10.1021/ol061847o