{(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol

Base Information

• Chemical Name: {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol
• CAS No.: 131311-08-5
• Molecular Formula: C₂₆H₄₂O₆Si
• Molecular Weight: 478.701

Synonyms:{(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol

Chemical Property of {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol

There total 18 articles about {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol 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: 97.0%

(E)-4-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol (131311-07-4) → {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol (131311-08-5)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; water; at 0 ℃; for 0.5h;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

2-deoxy-D-ribose (22900-10-3,35536-75-5,36792-85-5,113890-34-9,113890-37-2,133813-23-7) → {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol (131311-08-5)

Guidance literature:

Multi-step reaction with 17 steps

1: 97 percent / tetrahydrofuran / 3 h / Heating

2: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

3: 89 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

4: 84 percent / hexane; CH₂Cl₂ / 2 h / -20 °C

5: 100 percent / CH₂Cl₂ / 0.25 h / 25 °C

6: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

7: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -25 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

8: 93 percent / triethylamine, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

9: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.58 h / 0 °C

10: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

11: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 0 °C

12: 95 percent / imidazole / dimethylformamide / 12 h / 50 °C

13: 1.) 9-BBN, 2.) 3N NaOH, H₂O₂ / 1.) THF, 25 deg C, 40 min, 2.) 30 min

14: 95 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

15: 90 percent / benzoic acid / benzene / 0.5 h / 50 °C

16: 97 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

17: 97 percent / m-Chloroperbenzoic acid / CH₂Cl₂; H₂O / 0.5 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; benzoic acid; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)85579-4

Reference yield:

benzaldehyde dimethyl acetal (1125-88-8) → {(2R,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxiranyl}-methanol (131311-08-5)

Guidance literature:

Multi-step reaction with 16 steps

1: 96 percent / camphorsulfonic acid / CH₂Cl₂ / 12 h / 25 °C

2: 89 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 1 h / -78 °C

3: 84 percent / hexane; CH₂Cl₂ / 2 h / -20 °C

4: 100 percent / CH₂Cl₂ / 0.25 h / 25 °C

5: 96 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

6: 1.) diethyl-D-tartrate, titanium(IV) isopropoxide, 2.) tert-butylhydroperoxide / 1.) CH₂Cl₂, -25 deg C, 30 min, 2.) 2,2,4-trimethylpentane, -20 deg C, 14 h

7: 93 percent / triethylamine, SO₃*pyridine / CH₂Cl₂; dimethylsulfoxide / 2 h / 0 °C

8: 88 percent / NaN(SiMe₃)2 / tetrahydrofuran / 0.58 h / 0 °C

9: 95 percent / tetrabutylammonium fluoride / tetrahydrofuran / 0.33 h / 25 °C

10: 94 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 12 h / 0 °C

11: 95 percent / imidazole / dimethylformamide / 12 h / 50 °C

12: 1.) 9-BBN, 2.) 3N NaOH, H₂O₂ / 1.) THF, 25 deg C, 40 min, 2.) 30 min

13: 95 percent / oxalyl chloride, DMSO / CH₂Cl₂ / 0.67 h / -78 °C

14: 90 percent / benzoic acid / benzene / 0.5 h / 50 °C

15: 97 percent / DIBAL / CH₂Cl₂ / 0.25 h / -78 °C

16: 97 percent / m-Chloroperbenzoic acid / CH₂Cl₂; H₂O / 0.5 h / 0 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; diethyl (2S,3S)-tartrate; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; dihydrogen peroxide; sodium hexamethyldisilazane; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; 3-chloro-benzenecarboperoxoic acid; benzoic acid; In tetrahydrofuran; hexane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

DOI:10.1016/S0040-4020(01)85579-4

upstream raw materials:

(E)-4-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yl]-2-methyl-but-2-en-1-ol

2-deoxy-D-ribose

benzaldehyde dimethyl acetal

(E)-(5S,6R)-5,6,7-Trihydroxy-2-methyl-hept-2-enoic acid ethyl ester

Downstream raw materials:

(2S,3R)-3-[(2R,4aR,6S,7R,8aS)-7-(tert-Butyl-dimethyl-silanyloxy)-4a,6-dimethyl-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-ylmethyl]-2-methyl-oxirane-2-carbaldehyde

(2R,4aR,6S,7R,8aS)-4a,6-Dimethyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-ol

(2R,4aR,6R,7S,8aR,9aS,10aS)-4a,7,10a-Trimethyl-2-phenyl-7-vinyl-octahydro-1,3,8,10-tetraoxa-anthracen-6-ol

tert-Butyl-[(2R,4aR,6S,7R,8aS)-4a,6-dimethyl-6-((2R,3R)-3-methyl-3-vinyl-oxiranylmethyl)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy]-dimethyl-silane

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