11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid

Base Information

• Chemical Name: 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid
• CAS No.: 287945-09-9
• Molecular Formula: C₆₃H₈₆O₁₅
• Molecular Weight: 1083.37
• Mol file: 287945-09-9.mol

Synonyms:11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid

Chemical Property of 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid

There total 27 articles about 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid 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:

C78H96O17 (261926-73-2) → 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid (287945-09-9)

Guidance literature:

With potassium hydroxide; In methanol; at 40 ℃;

DOI:10.1016/S0040-4039(00)00427-5

Reference yield:

(11S)-11-hydroxytetradecanoic acid methyl ester (152427-52-6) → 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid (287945-09-9)

Guidance literature:

Multi-step reaction with 5 steps

1: NIS; TfOH; 4 Angstroem MS / CH₂Cl₂ / -20 °C

2: NaOMe / methanol

3: NaBH₄ / dimethylformamide / 70 °C

4: 71 percent / NIS; TfOH; 4 Angstroem MS / CH₂Cl₂ / -20 °C

5: KOH / methanol / 40 °C

With potassium hydroxide; sodium tetrahydroborate; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 Angstroem MS; sodium methylate; In methanol; dichloromethane; N,N-dimethyl-formamide; 1: glycosylation / 2: Deacetylation / 3: Hydrogenolysis / 4: glucosylation / 5: Hydrolysis;

DOI:10.1016/S0040-4039(00)00427-5

Reference yield:

(2S)-2,5-dihydroxy-1-tosyloxypentane (89872-57-1) → 11-{3-[4-(4-allyloxy-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-5-benzyloxy-3-hydroxy-6-methyl-tetrahydro-pyran-2-yloxy]-4,5-bis-benzyloxy-6-methyl-tetrahydro-pyran-2-yloxy}-tetradecanoic acid (287945-09-9)

Guidance literature:

Multi-step reaction with 16 steps

1.1: pyridine / CH₂Cl₂

2.1: tert-BuOK / tetrahydrofuran

3.1: CuI / tetrahydrofuran / 0 °C

4.1: pyridine

5.1: n-Bu₄NF / tetrahydrofuran

6.1: CBr₄; Ph₃P / dimethylformamide

7.1: Bu₃SnH; AIBN / toluene / 80 °C

8.1: NaOMe / methanol / 70 °C

9.1: Na; liq. NH₃ / -80 °C

10.1: TEMPO; TBACl; NCS / CH₂Cl₂; H₂O / pH 8.6

10.2: NaClO₂; NaH₂PO₄ / 2-methyl-propan-2-ol; various solvent(s); H₂O

11.1: diethyl ether

12.1: NIS; TfOH; 4 Angstroem MS / CH₂Cl₂ / -20 °C

13.1: NaOMe / methanol

14.1: NaBH₄ / dimethylformamide / 70 °C

15.1: 71 percent / NIS; TfOH; 4 Angstroem MS / CH₂Cl₂ / -20 °C

16.1: KOH / methanol / 40 °C

With pyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; potassium hydroxide; sodium tetrahydroborate; N-chloro-succinimide; N-iodo-succinimide; copper(l) iodide; 2,2'-azobis(isobutyronitrile); carbon tetrabromide; trifluorormethanesulfonic acid; 4 Angstroem MS; potassium tert-butylate; tetrabutyl ammonium fluoride; tetrabutyl-ammonium chloride; ammonia; tri-n-butyl-tin hydride; sodium methylate; sodium; triphenylphosphine; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1.1: Etherification / 2.1: Cyclization / 3.1: Grignard reaction / 4.1: Esterification / 5.1: Elimination / 6.1: Bromination / 7.1: Reduction / 8.1: Hydrolysis / 9.1: Birch reduction / 10.1: Oxidation / 10.2: Oxidation / 11.1: Esterification / 12.1: glycosylation / 13.1: Deacetylation / 14.1: Hydrogenolysis / 15.1: glucosylation / 16.1: Hydrolysis;

DOI:10.1016/S0040-4039(00)00427-5

upstream raw materials:

C₇₈H₉₆O₁₇

(2S)-2,5-dihydroxy-1-tosyloxypentane

(11S)-11-hydroxytetradecanoic acid methyl ester

(2S)-5-(tert-butyldiphenylsilyloxy)-1,2-epoxypentane

Downstream raw materials:

C₆₃H₈₄O₁₄

Refernces