methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Base Information

• Chemical Name: methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate
• CAS No.: 213319-95-0
• Molecular Formula: C₂₁H₂₈O₆S₂
• Molecular Weight: 440.582
• Mol file: 213319-95-0.mol

Synonyms:methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Chemical Property of methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

There total 21 articles about methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate 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:

(E)-2-methyl-2-buten-1-ol (497-02-9) → methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate (213319-95-0)

Guidance literature:

Multi-step reaction with 16 steps

1.1: diisopropyl D-tartrate; 3-Angstroem molecular sieves; cumene hydroperoxide / titanium(IV) isopropoxide / CH₂Cl₂ / 13 h / -78 - -70 °C

2.1: 4-Angstroem molecular sieves; 4-methylmorpholine N-oxide / tetrapropylammonium perruthenate / acetonitrile / 1 h / 20 °C

3.1: LiCl; i-Pr₂NEt / acetonitrile / 1 h / 0 °C

4.1: Bu₃P; Et₃N; HCO₂H / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-chloroform adduct / dioxane / 9.5 h / 20 °C

4.2: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

5.1: 59.7 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

6.1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

7.1: 79 percent / Bu₄NF / tetrahydrofuran / 21 h / 20 - 30 °C

8.1: 88 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 0 - 20 °C

9.1: 87 percent / Ph₃P / Pd(OAc)2 / dimethylformamide / 6.5 h / 90 °C

10.1: 76 percent / LiI / dimethylformamide / 5 h / Heating

11.1: O₃ / methanol / 0.25 h / -78 °C

11.2: Me₂S / methanol / 1 h / -78 - 20 °C

12.1: 168 mg / conc. HCl / CH₂Cl₂ / 15 h / 20 °C

13.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

14.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 - 0 °C

14.2: tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

15.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

16.1: 185 mg / DMAP; pyridine / 8.25 h / 0 - 20 °C

With pyridine; hydrogenchloride; dmap; formic acid; tributylphosphine; Cumene hydroperoxide; 3 A molecular sieve; 4 A molecular sieve; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; D-(-)-diisopropyl tartrate; ozone; 4-methylmorpholine N-oxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; lithium iodide; lithium diisopropyl amide; titanium(IV) isopropylate; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; tetrapropylammonium perruthennate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Sharpless epoxidation / 2.1: Oxidation / 3.1: Masamune-Roush olefination / 4.1: Catalytic hydrogenation / 4.2: silylation / 5.1: Reduction / 6.1: Acylation / 7.1: desilylation / 8.1: Esterification / 9.1: Cyclization / 10.1: Decarboxylation / 11.1: ozonolysis / 11.2: Decomposition / 12.1: Isomerization / 13.1: Cyclization / 14.1: Metallation / 14.2: Addition / 15.1: Methylation / 16.1: Acylation;

DOI:10.1021/jo9805246

Reference yield:

(2S,3R)-2,3-Dimethyl-oxirane-2-carbaldehyde (358750-37-5) → methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate (213319-95-0)

Guidance literature:

Multi-step reaction with 14 steps

1.1: LiCl; i-Pr₂NEt / acetonitrile / 1 h / 0 °C

2.1: Bu₃P; Et₃N; HCO₂H / tris(dibenzylideneacetone)dipalladium⁽⁰⁾-chloroform adduct / dioxane / 9.5 h / 20 °C

2.2: 2,6-lutidine / CH₂Cl₂ / 3 h / 0 °C

3.1: 59.7 mg / DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

5.1: 79 percent / Bu₄NF / tetrahydrofuran / 21 h / 20 - 30 °C

6.1: 88 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 0 - 20 °C

7.1: 87 percent / Ph₃P / Pd(OAc)2 / dimethylformamide / 6.5 h / 90 °C

8.1: 76 percent / LiI / dimethylformamide / 5 h / Heating

9.1: O₃ / methanol / 0.25 h / -78 °C

9.2: Me₂S / methanol / 1 h / -78 - 20 °C

10.1: 168 mg / conc. HCl / CH₂Cl₂ / 15 h / 20 °C

11.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

12.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 - 0 °C

12.2: tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

13.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

14.1: 185 mg / DMAP; pyridine / 8.25 h / 0 - 20 °C

With pyridine; hydrogenchloride; dmap; formic acid; tributylphosphine; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; lithium chloride; lithium iodide; lithium diisopropyl amide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; palladium diacetate; In tetrahydrofuran; 1,4-dioxane; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Masamune-Roush olefination / 2.1: Catalytic hydrogenation / 2.2: silylation / 3.1: Reduction / 4.1: Acylation / 5.1: desilylation / 6.1: Esterification / 7.1: Cyclization / 8.1: Decarboxylation / 9.1: ozonolysis / 9.2: Decomposition / 10.1: Isomerization / 11.1: Cyclization / 12.1: Metallation / 12.2: Addition / 13.1: Methylation / 14.1: Acylation;

DOI:10.1021/jo9805246

Reference yield:

(+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate (213319-90-5) → methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(1,3-dithiolan-2-yl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate (213319-95-0)

Guidance literature:

Multi-step reaction with 15 steps

1.1: 100 percent / imidazole / dimethylformamide / 10 h / 20 °C

2.1: 100 percent / Et₃SiH / Pd-C / acetone / 0.25 h / 0 - 20 °C

3.1: 94 percent / LiCl; DBU / acetonitrile / 1 h / 0 °C

4.1: 100 percent / DIBALH / tetrahydrofuran; hexane / 1 h / -78 °C

5.1: 98 percent / pyridine / CH₂Cl₂ / 1 h / 0 °C

6.1: 79 percent / Bu₄NF / tetrahydrofuran / 21 h / 20 - 30 °C

7.1: 88 percent / DMAP; 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride / CH₂Cl₂ / 24 h / 0 - 20 °C

8.1: 87 percent / Ph₃P / Pd(OAc)2 / dimethylformamide / 6.5 h / 90 °C

9.1: 76 percent / LiI / dimethylformamide / 5 h / Heating

10.1: O₃ / methanol / 0.25 h / -78 °C

10.2: Me₂S / methanol / 1 h / -78 - 20 °C

11.1: 168 mg / conc. HCl / CH₂Cl₂ / 15 h / 20 °C

12.1: 100 percent / BF₃*Et₂O / CH₂Cl₂ / 0.5 h / 0 °C

13.1: LDA / tetrahydrofuran; hexane / 0.42 h / -78 - 0 °C

13.2: tetrahydrofuran; hexane / 2.5 h / -78 - 0 °C

14.1: 10-camphorsulfonic acid / CH₂Cl₂; methanol / 1 h / 20 °C

15.1: 185 mg / DMAP; pyridine / 8.25 h / 0 - 20 °C

With pyridine; 1H-imidazole; hydrogenchloride; triethylsilane; dmap; boron trifluoride diethyl etherate; (1S)-10-camphorsulfonic acid; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; ozone; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triphenylphosphine; lithium chloride; lithium iodide; lithium diisopropyl amide; palladium diacetate; palladium on activated charcoal; In tetrahydrofuran; methanol; hexane; dichloromethane; N,N-dimethyl-formamide; acetone; acetonitrile; 1.1: silylation / 2.1: Reduction / 3.1: Masamune-Roush olefination / 4.1: Reduction / 5.1: Acylation / 6.1: desilylation / 7.1: Esterification / 8.1: Cyclization / 9.1: Decarboxylation / 10.1: ozonolysis / 10.2: Decomposition / 11.1: Isomerization / 12.1: Cyclization / 13.1: Metallation / 13.2: Addition / 14.1: Methylation / 15.1: Acylation;

DOI:10.1021/jo9805246

upstream raw materials:

((2R,4R,5R,6R)-4-[1,3]Dithiolan-2-yl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-hydroxy-acetic acid methyl ester

benzoyl chloride

(E)-2-methyl-2-buten-1-ol

(2S,3R)-2,3-Dimethyl-oxirane-2-carbaldehyde

Downstream raw materials:

Benzoic acid ((2R,4R,5R,6R)-4-formyl-2-methoxy-5,6-dimethyl-tetrahydro-pyran-2-yl)-methoxycarbonyl-methyl ester

methyl (2R,4R,5R,6R)-[5,6-dimethyl-4-(hydroxymethyl)-2-methoxytetrahydropyranyl]-2-O-benzoylglycolate

Benzoic acid methoxycarbonyl-((2R,5R,6R)-2-methoxy-5,6-dimethyl-4-methylene-tetrahydro-pyran-2-yl)-methyl ester

Benzoic acid methoxycarbonyl-[(2R,4R,5R,6R)-2-methoxy-5,6-dimethyl-4-(2-nitro-phenylselanylmethyl)-tetrahydro-pyran-2-yl]-methyl ester