(3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one

Base Information

• Chemical Name: (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one
• CAS No.: 259258-22-5
• Molecular Formula: C₂₀H₂₈O₇
• Molecular Weight: 380.438
• Mol file: 259258-22-5.mol

Synonyms:(3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one

Chemical Property of (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one

There total 21 articles about (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one 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:

(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine (109958-35-2) → (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one (259258-22-5)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

2.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

3.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

4.1: DIBALH / CH₂Cl₂; hexane / 1 h / -78 °C

4.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

5.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

6.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

7.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

7.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

8.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

9.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

10.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

11.1: N-iodosuccinimide / acetonitrile; H₂O / 0.17 h / 20 °C

12.1: potassium tert-butoxide / tetrahydrofuran / 0.75 h / 20 °C

12.2: 30.5 g / tetrahydrofuran / -78 - 0 °C

13.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

14.1: pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

15.1: 7.49 g / sodium borohydride / methanol / 0.17 h / 0 °C

16.1: 92 percent / D-(-)-diethyl tartrate; tert-butyl hydroperoxide; titanium tetraisopropoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3 h / -20 °C

17.1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

18.1: 5.39 g / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; dipyridinium dichromate; 2-methyl-but-2-ene; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; water; dimethyl sulfoxide; acetonitrile; tert-butyl alcohol; 1.1: Hydrolysis / 2.1: Tosylation / 3.1: Substitution / 4.1: Reduction / 4.2: Hydrolysis / 5.1: Oxidation / 6.1: Cyclization / 7.1: Metallation / 7.2: Methylation / 8.1: Metallation / 9.1: Ring cleavage / 10.1: Etherification / 11.1: Oxidation / 12.1: Metallation / 12.2: olefination; Horner-Emmons reaction / 13.1: Reduction / 14.1: Oxidation / 15.1: Reduction / 16.1: Epoxidation / 17.1: Etherification / 18.1: Hydrolysis;

DOI:10.1021/jo990988j

Reference yield:

benzyl bromide (100-39-0) → (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one (259258-22-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

4.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

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

5.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

6.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

7.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

8.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

12.1: N-iodosuccinimide / acetonitrile; H₂O / 0.17 h / 20 °C

13.1: potassium tert-butoxide / tetrahydrofuran / 0.75 h / 20 °C

13.2: 30.5 g / tetrahydrofuran / -78 - 0 °C

14.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

15.1: pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

16.1: 7.49 g / sodium borohydride / methanol / 0.17 h / 0 °C

17.1: 92 percent / D-(-)-diethyl tartrate; tert-butyl hydroperoxide; titanium tetraisopropoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3 h / -20 °C

18.1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

19.1: 5.39 g / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; dipyridinium dichromate; 2-methyl-but-2-ene; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Substitution / 5.1: Reduction / 5.2: Hydrolysis / 6.1: Oxidation / 7.1: Cyclization / 8.1: Metallation / 8.2: Methylation / 9.1: Metallation / 10.1: Ring cleavage / 11.1: Etherification / 12.1: Oxidation / 13.1: Metallation / 13.2: olefination; Horner-Emmons reaction / 14.1: Reduction / 15.1: Oxidation / 16.1: Reduction / 17.1: Epoxidation / 18.1: Etherification / 19.1: Hydrolysis;

DOI:10.1021/jo990988j

Reference yield:

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside (68907-47-1) → (3R,4R,5R)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-hydroxy-3-methyl-dihydro-furan-2-one (259258-22-5)

Guidance literature:

Multi-step reaction with 19 steps

1.1: 99 percent / tetra-n-butylammonium iodide; sodium hydride / tetrahydrofuran; dimethylformamide; various solvent(s) / 20 °C

2.1: 98 percent / p-toluenesulfonic acid monohydrate / methanol / 1.5 h / 20 °C

3.1: 47.10 g / 4-(dimethylamino)pyridine; triethylamine / CH₂Cl₂ / 4 h / 0 °C

4.1: 70 percent / dimethylsulfoxide / 1.5 h / 70 °C

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

5.2: 12.38 g / HCl / CH₂Cl₂; hexane; H₂O / 0.25 h

6.1: 14.79 g / 2-methyl-2-butene; NaH₂PO₄*H₂O; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 0.33 h / 20 °C

7.1: 8.03 g / triethylamine; phenylsulfonyl chloride / CH₂Cl₂ / 0 - 20 °C

8.1: LiHMDS / tetrahydrofuran; hexane / 0.5 h / -78 °C

8.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

9.1: 23.46 g / lithium diisopropylamide / tetrahydrofuran; hexane / 0.33 h / -78 °C

10.1: 91 percent / trimethylsilyl triflate / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 98 percent / 2,6-lutidine / CH₂Cl₂ / 2.5 h / 20 °C

12.1: N-iodosuccinimide / acetonitrile; H₂O / 0.17 h / 20 °C

13.1: potassium tert-butoxide / tetrahydrofuran / 0.75 h / 20 °C

13.2: 30.5 g / tetrahydrofuran / -78 - 0 °C

14.1: DIBALH / CH₂Cl₂; hexane / 0.5 h / -78 °C

15.1: pyridinium dichromate; molecular sieves 4A / CH₂Cl₂ / 2 h / 20 °C

16.1: 7.49 g / sodium borohydride / methanol / 0.17 h / 0 °C

17.1: 92 percent / D-(-)-diethyl tartrate; tert-butyl hydroperoxide; titanium tetraisopropoxide / molecular sieves 4A / CH₂Cl₂; 2,2,4-trimethyl-pentane / 3 h / -20 °C

18.1: 95 percent / N,N-diisopropylethylamine / CH₂Cl₂ / 20 °C

19.1: 5.39 g / tetra-n-butylammonium fluoride; acetic acid / tetrahydrofuran / 1 h / 20 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; dmap; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; N-iodo-succinimide; dipyridinium dichromate; 2-methyl-but-2-ene; diethyl (2S,3S)-tartrate; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; potassium tert-butylate; tetrabutyl ammonium fluoride; tetra-(n-butyl)ammonium iodide; sodium hydride; diisobutylaluminium hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; N-ethyl-N,N-diisopropylamine; benzenesulfonyl chloride; lithium hexamethyldisilazane; lithium diisopropyl amide; 4 A molecular sieve; In tetrahydrofuran; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 1.1: Alkylation / 2.1: Hydrolysis / 3.1: Tosylation / 4.1: Substitution / 5.1: Reduction / 5.2: Hydrolysis / 6.1: Oxidation / 7.1: Cyclization / 8.1: Metallation / 8.2: Methylation / 9.1: Metallation / 10.1: Ring cleavage / 11.1: Etherification / 12.1: Oxidation / 13.1: Metallation / 13.2: olefination; Horner-Emmons reaction / 14.1: Reduction / 15.1: Oxidation / 16.1: Reduction / 17.1: Epoxidation / 18.1: Etherification / 19.1: Hydrolysis;

DOI:10.1021/jo990988j

upstream raw materials:

(3R,4R,5S)-5-[(1S,2S)-1-Benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-(tert-butyl-dimethyl-silanyloxy)-3-methyl-dihydro-furan-2-one

(2R,4aR,6S,7S,8S,8aS)-8-Benzyloxy-6-methoxy-7-methyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine

methyl 4,6-O-benzylidene-2-deoxy-2-C-methyl-α-D-altro-pyranoside

benzyl bromide

Downstream raw materials:

(2R,3R,4R,5R)-5-Allyloxy-2-[(1S,2S)-1-benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-methyl-tetrahydro-furan-3-ol

(2R,3R,4R,5S)-5-Allyloxy-2-[(1S,2S)-1-benzyloxy-2-((2R,3R)-3-methoxymethoxymethyl-oxiranyl)-propyl]-4-methyl-tetrahydro-furan-3-ol