1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one

Base Information

• Chemical Name: 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one
• CAS No.: 84170-95-6
• Molecular Formula: C₁₅H₂₆O₆
• Molecular Weight: 302.368
• Mol file: 84170-95-6.mol

Synonyms:

Chemical Property of 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one

There total 12 articles about 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-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:

(1aR,3aS,6S,7aS,7bR)-6-Phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene (84109-51-3) → 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one (66262-70-2,84170-95-6)

Guidance literature:

Multi-step reaction with 7 steps

1: 43 percent / CuI / tetrahydrofuran / 0.17 h / -30 °C

2: 97 percent / 1N HCl / dioxane; H₂O / 6 h / Ambient temperature

3: 77 percent / 0.5percent H₂SO₄, molecular sieve 4 Angstroem / 0.33 h / Ambient temperature

4: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

5: 94.5 percent / 18-crown-6 / hexamethylphosphoric acid triamide / 12 h / Ambient temperature

6: Ni(acac)2 / toluene / 6 h / 0 °C

7: MCPBA / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; dmap; bis(acetylacetonate)nickel(II); copper(l) iodide; 18-crown-6 ether; 4 A molecular sieve; sulfuric acid; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; toluene;

DOI:10.1021/ja00341a052

Reference yield:

C27H28O9S2 (84170-90-1) → 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one (66262-70-2,84170-95-6)

Guidance literature:

Multi-step reaction with 8 steps

1: MeONa / CH₂Cl₂ / 24 h / Ambient temperature

2: 43 percent / CuI / tetrahydrofuran / 0.17 h / -30 °C

3: 97 percent / 1N HCl / dioxane; H₂O / 6 h / Ambient temperature

4: 77 percent / 0.5percent H₂SO₄, molecular sieve 4 Angstroem / 0.33 h / Ambient temperature

5: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

6: 94.5 percent / 18-crown-6 / hexamethylphosphoric acid triamide / 12 h / Ambient temperature

7: Ni(acac)2 / toluene / 6 h / 0 °C

8: MCPBA / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; dmap; bis(acetylacetonate)nickel(II); copper(l) iodide; 18-crown-6 ether; 4 A molecular sieve; sulfuric acid; sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; toluene;

DOI:10.1021/ja00341a052

Reference yield:

(2S,4aS,7R,8S,8aR)-2-Phenyl-hexahydro-pyrano[3,2-d][1,3]dioxine-7,8-diol (84170-89-8) → 1-{(2S,3R,4R,5S)-3,4-Dihydroxy-5-[(2R,3R)-3-((1S,2S)-2-hydroxy-1-methyl-propyl)-oxiranylmethyl]-tetrahydro-pyran-2-yl}-propan-2-one (66262-70-2,84170-95-6)

Guidance literature:

Multi-step reaction with 9 steps

1: 70 percent / pyridine

2: MeONa / CH₂Cl₂ / 24 h / Ambient temperature

3: 43 percent / CuI / tetrahydrofuran / 0.17 h / -30 °C

4: 97 percent / 1N HCl / dioxane; H₂O / 6 h / Ambient temperature

5: 77 percent / 0.5percent H₂SO₄, molecular sieve 4 Angstroem / 0.33 h / Ambient temperature

6: 96 percent / Et₃N, DMAP / CH₂Cl₂ / 1.5 h / Ambient temperature

7: 94.5 percent / 18-crown-6 / hexamethylphosphoric acid triamide / 12 h / Ambient temperature

8: Ni(acac)2 / toluene / 6 h / 0 °C

9: MCPBA / CH₂Cl₂ / 1.5 h / Ambient temperature

With hydrogenchloride; dmap; bis(acetylacetonate)nickel(II); copper(l) iodide; 18-crown-6 ether; 4 A molecular sieve; sulfuric acid; sodium methylate; triethylamine; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; 1,4-dioxane; pyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane; water; toluene;

DOI:10.1021/ja00341a052

upstream raw materials:

1-[(2S,3R,4R,5S)-3,4-Dihydroxy-5-((E)-(4R,5S)-5-hydroxy-4-methyl-hex-2-enyl)-tetrahydro-pyran-2-yl]-propan-2-one

(1aR,3aS,6S,7aS,7bR)-6-Phenyl-hexahydro-1,3,5,7-tetraoxa-cyclopropa[a]naphthalene

[(3aS,4S,7S,7aR)-7-((E)-(4R,5S)-5-Hydroxy-4-methyl-hex-2-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-yl]-acetonitrile

Toluene-4-sulfonic acid (3aR,4S,7S,7aR)-7-((E)-(4R,5S)-5-hydroxy-4-methyl-hex-2-enyl)-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-4-ylmethyl ester