(2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

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Chemical Name:(2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran
CAS No.:1616868-85-9
Molecular Formula:C₄₃H₆₆O₄
Molecular Weight:646.995
Hs Code.:

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Chemical Property of (2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

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Technology Process of (2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

There total 26 articles about (2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran 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%

: C₄₄H₆₈O₅

: 1616868-85-9
(2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

Guidance literature:: With 2,2'-azobis(isobutyronitrile); tri-n-butyl-tin hydride; In toluene; for 1h; Reflux;
DOI:10.1016/j.tetlet.2014.02.096

Reference yield:

: 91548-58-2
ethyl (2E)-3-{(4R,5R)-5-[(benzyloxy)methyl]-2,2-dimethyl-1,3-dioxolan-4-yl}acrylate

: 1616868-85-9
(2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 17 steps

1.1: nickel(II) chloride hexahydrate; sodium tetrahydroborate; methanol / 0 - 20 °C

2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0 - 20 °C

3.1: oxalyl dichloride; triethylamine; dimethyl sulfoxide / dichloromethane / -78 °C

4.1: benzene / 6 h / 20 °C

5.1: diisobutylaluminium hydride / dichloromethane / 2 h / -20 - 20 °C

6.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 12 h / -25 °C / Molecular sieve

7.1: camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C

7.2: 2 h / 20 °C

8.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

9.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 2 h

10.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C

11.1: magnesium / tetrahydrofuran / 2 h / -78 - 25 °C

12.1: sodium hydride / tetrahydrofuran / 6 h / 0 - 20 °C

13.1: toluene-4-sulfonic acid; methanol / 2 h / 20 °C

14.1: sodium periodate / tetrahydrofuran; water

15.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

15.2: 0.5 h / 0 - 20 °C

16.1: sodium hydride; carbon disulfide / tetrahydrofuran / 6 h / Reflux

17.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / Reflux

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; carbon disulfide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; nickel(II) chloride hexahydrate; 2,2'-azobis(isobutyronitrile); diethyl (2R,3R)-tartrate; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; magnesium; dimethyl sulfoxide; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; benzene; 3.1: |Swern Oxidation / 6.1: |Sharpless Asymmetric Epoxidation / 16.1: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.tetlet.2014.02.096

Reference yield:

: 1616868-92-8
(E)-ethyl 5-((4R,5R)-5-((benzyloxy)methyl)-2,2-dimethyl-1,3-dioxolan-4-yl)pent-2-enoate

: 1616868-85-9
(2S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran

Guidance literature:: Multi-step reaction with 13 steps

1.1: diisobutylaluminium hydride / dichloromethane / 2 h / -20 - 20 °C

2.1: diethyl (2R,3R)-tartrate; titanium(IV) isopropylate; tert.-butylhydroperoxide / dichloromethane / 12 h / -25 °C / Molecular sieve

3.1: camphor-10-sulfonic acid / dichloromethane / 0.08 h / 0 °C

3.2: 2 h / 20 °C

4.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C

5.1: triethylamine; di(n-butyl)tin oxide / dichloromethane / 2 h

6.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C

7.1: magnesium / tetrahydrofuran / 2 h / -78 - 25 °C

8.1: sodium hydride / tetrahydrofuran / 6 h / 0 - 20 °C

9.1: toluene-4-sulfonic acid; methanol / 2 h / 20 °C

10.1: sodium periodate / tetrahydrofuran; water

11.1: trifluoroacetic acid / dichloromethane / 3 h / 0 - 20 °C

11.2: 0.5 h / 0 - 20 °C

12.1: sodium hydride; carbon disulfide / tetrahydrofuran / 6 h / Reflux

13.1: tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile) / toluene / 1 h / Reflux

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; carbon disulfide; sodium periodate; 2,2'-azobis(isobutyronitrile); diethyl (2R,3R)-tartrate; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; tri-n-butyl-tin hydride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; magnesium; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; water; ethyl acetate; toluene; 2.1: |Sharpless Asymmetric Epoxidation / 12.1: |Barton-McCombie Deoxygenation;
DOI:10.1016/j.tetlet.2014.02.096