(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

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Chemical Name:(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol
CAS No.:1616868-99-5
Molecular Formula:C₄₃H₆₆O₅
Molecular Weight:662.994
Hs Code.:

Synonyms:(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

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Chemical Property of (2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

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Technology Process of (2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

There total 22 articles about (2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-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: 55.0%

: 1616868-86-0
C₂₅H₄₀O₃

: 1616868-87-1
(4S,5S)-5-(benzyloxy)undeca-1,10-dien-4-ol

: 1616868-99-5
(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

Guidance literature:: C₂₅H₄₀O₃; (4S,5S)-5-(benzyloxy)undeca-1,10-dien-4-ol; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 3h;

With methanol; potassium carbonate; at 0 - 20 ℃; for 0.5h;
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

: 1616868-99-5
(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

Guidance literature:: Multi-step reaction with 15 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

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium tetrahydroborate; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; nickel(II) chloride hexahydrate; diethyl (2R,3R)-tartrate; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; 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; benzene; 3.1: |Swern Oxidation / 6.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.02.096

Reference yield:

: 1616868-90-6
C₁₈H₂₆O₅

: 1616868-99-5
(2S,4S,6R)-2-((S)-1-(benzyloxy)hept-6-enyl)-6-((2R,5R)-5-((R)-1-(benzyloxy)tridecyl)-tetrahydrofuran-2-yl)-tetrahydro-2H-pyran-4-ol

Guidance literature:: Multi-step reaction with 14 steps

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

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

3.1: benzene / 6 h / 20 °C

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

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

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

6.2: 2 h / 20 °C

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

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

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

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

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

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

13.1: sodium periodate / tetrahydrofuran; water

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

14.2: 0.5 h / 0 - 20 °C

With titanium(IV) isopropylate; methanol; tert.-butylhydroperoxide; sodium periodate; lithium aluminium tetrahydride; oxalyl dichloride; diethyl (2R,3R)-tartrate; palladium 10% on activated carbon; camphor-10-sulfonic acid; hydrogen; 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; benzene; 2.1: |Swern Oxidation / 5.1: |Sharpless Asymmetric Epoxidation;
DOI:10.1016/j.tetlet.2014.02.096