(E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester

Base Information

• Chemical Name: (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester
• CAS No.: 170706-60-2
• Molecular Formula: C₃₆H₅₂O₇Si
• Molecular Weight: 624.89

Synonyms:(E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester

Chemical Property of (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester

There total 8 articles about (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester 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:

tert-Butyl-dimethyl-((2R,4aR,6S,7R,8aS)-6-methyl-2-phenyl-6-vinyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yloxy)-silane (131310-62-8) → (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester (170706-60-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 92 percent / CSA / methanol / 1 h / 0 °C

2: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

3: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

4: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

5: 90 percent / benzene / 1 h / 50 °C

6: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

7: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

8: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

9: 90 percent / PhCO₂H / benzene / 0.5 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; camphor-10-sulfonic acid; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00146a008

Reference yield:

(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-methyl-6-vinyl-tetrahydro-pyran-3-ol (170706-52-2) → (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester (170706-60-2)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / KH / tetrahydrofuran / 1 h / 45 °C

2: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

3: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

4: 90 percent / benzene / 1 h / 50 °C

5: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

6: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

7: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

8: 90 percent / PhCO₂H / benzene / 0.5 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; dihydrogen peroxide; potassium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00146a008

Reference yield:

((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane (170706-53-3) → (E)-3-{(2R,3R)-3-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-2-methyl-acrylic acid ethyl ester (170706-60-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 1.) 9-BBN, 2.) 3 N NaOH, 30percent aq. H₂O₂ / 1.) THF, 25 deg C, 1.5 h, 2.) THF, 0 deg C, 1 h

2: 96 percent / (COCl)2, DMSO, Et₃N / CH₂Cl₂ / 1 h / -78 °C

3: 90 percent / benzene / 1 h / 50 °C

4: 96 percent / DIBALH / CH₂Cl₂ / 0.5 h / -78 °C

5: 92 percent / (-)-diethyl tartrate, Ti(O-i-Pr)4, tert-BuOOH / CH₂Cl₂ / 14 h / -25 °C

6: 94 percent / SO₃*pyridine, Et₃N / CH₂Cl₂; dimethylsulfoxide / 4 h / 0 °C

7: 90 percent / PhCO₂H / benzene / 0.5 h / 25 °C

With titanium(IV) isopropylate; tert.-butylhydroperoxide; sodium hydroxide; 9-borabicyclo[3.3.1]nonane dimer; oxalyl dichloride; pyridine-SO₃ complex; dihydrogen peroxide; diisobutylaluminium hydride; dimethyl sulfoxide; (-)-diethyl tartrate; triethylamine; benzoic acid; In dichloromethane; dimethyl sulfoxide; benzene;

DOI:10.1021/ja00146a008

upstream raw materials:

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

(2R,3S,5R,6S)-5-(tert-Butyl-dimethyl-silanyloxy)-2-hydroxymethyl-6-methyl-6-vinyl-tetrahydro-pyran-3-ol

2-[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-(tert-butyl-dimethyl-silanyloxy)-2-methyl-tetrahydro-pyran-2-yl]-ethanol

((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-methyl-2-vinyl-tetrahydro-pyran-3-yloxy)-tert-butyl-dimethyl-silane

Downstream raw materials:

(E)-3-[(2R,3R)-3-((2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-3-hydroxy-2-methyl-tetrahydro-pyran-2-ylmethyl)-oxiranyl]-2-methyl-acrylic acid ethyl ester

(E)-3-((2S,3R,4aS,6R,7S,8aR)-7-Benzyloxy-6-benzyloxymethyl-3-hydroxy-4a-methyl-octahydro-pyrano[3,2-b]pyran-2-yl)-2-methyl-acrylic acid ethyl ester

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