(S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol

Base Information

• Chemical Name: (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol
• CAS No.: 1353031-25-0
• Molecular Formula: C₃₃H₄₆O₅
• Molecular Weight: 522.725
• Mol file: 1353031-25-0.mol

Synonyms:(S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol

Chemical Property of (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol

There total 13 articles about (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-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: 95.0%

1-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-Heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1353031-43-2) → (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol (1353031-25-0)

Guidance literature:

With lithium aluminium tetrahydride; lithium iodide; In diethyl ether; at -100 - -40 ℃;

DOI:10.1002/ejoc.201100888

Reference yield:

Octanal (124-13-0) → (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol (1353031-25-0)

Guidance literature:

Multi-step reaction with 10 steps

1.1: titanium(IV) isopropylate; (S)-[1,1']-binaphthalenyl-2,2'-diol / toluene / 36 h / -15 °C / Molecular sieve

2.1: ozone / dichloromethane / 0.08 h / -78 °C

2.2: 18 h / 20 °C

3.1: potassium tert-butylate / tetrahydrofuran / 4 h / 0 °C

4.1: magnesium / tetrahydrofuran; ethylene dibromide / 2 h / 20 °C

5.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

6.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 4 h / 20 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C

7.2: 24 h / 20 °C

8.1: potassium tert-butylate / tetrahydrofuran / 6 h / 4 °C

9.1: tetrahydrofuran / 0.5 h / 0 °C

10.1: lithium aluminium tetrahydride; lithium iodide / diethyl ether / -100 - -40 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; (S)-[1,1']-binaphthalenyl-2,2'-diol; ozone; magnesium; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium iodide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethylene dibromide; toluene; acetonitrile; 1.1: Keck allylation / 2.2: Wittig-Horner reaction / 7.1: Wittig-Horner reaction / 7.2: Wittig-Horner reaction / 8.1: Michael condensation;

DOI:10.1002/ejoc.201100888

Reference yield:

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one (1222190-49-9) → (S)-1-[(2S,4S,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-ol (1353031-25-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: lithium aluminium tetrahydride; lithium iodide / 0.5 h / -100 - -40 °C

2.1: 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide / 1,4-dioxane; water / 4 h / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 0.5 h / 20 °C

3.2: 24 h / 20 °C

4.1: potassium tert-butylate / tetrahydrofuran / 6 h / 4 °C

5.1: tetrahydrofuran / 0.5 h / 0 °C

6.1: lithium aluminium tetrahydride; lithium iodide / diethyl ether / -100 - -40 °C

With 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; lithium aluminium tetrahydride; potassium tert-butylate; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride; lithium iodide; In tetrahydrofuran; 1,4-dioxane; diethyl ether; water; acetonitrile; 3.1: Wittig-Horner reaction / 3.2: Wittig-Horner reaction / 4.1: Michael condensation;

DOI:10.1002/ejoc.201100888

upstream raw materials:

1-[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]pent-4-en-2-one

(S)-1-((2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl)pent-4-en-2-ol

(S,E)-6-[(2R,4S,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]-5-hydroxy-N-methoxy-N-methylhex-2-enamide

2-[(2R,4R,6R)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]-N-methoxy-N-methylacetamide

Downstream raw materials:

(S)-6-{[(2R,4R,6S)-6-{[(2R,4R,6R)-6-heptyl-2-phenyl-1,3-dioxan-4-yl]methyl}-2-phenyl-1,3-dioxan-4-yl]methyl}-5,6-dihydropyran-2-one

C₃₆H₄₈O₆