(E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester

Base Information

• Chemical Name: (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester
• CAS No.: 172427-44-0
• Molecular Formula: C₂₈H₄₄O₈Si
• Molecular Weight: 536.738

Synonyms:

Chemical Property of (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester

There total 9 articles about (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl 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:

((2S,3S,4S,5R,6R)-3-Allyloxy-4-benzyloxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester (172427-41-7) → (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester (172427-44-0)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) H₂; 2.) I₂ / 1.) 2MeP)2>PF₆ / 1.) THF; 2.) H₂O, RT

2: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

3: DIBALH / CH₂Cl₂ / -78 °C

4: toluene / Ambient temperature

5: 92 percent / DIBALH / CH₂Cl₂ / -78 °C

6: t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem MS / CH₂Cl₂ / -20 °C

7: SO₃*Pyr, Et₃N, DMSO / CH₂Cl₂ / 0 °C

8: toluene / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; hydrogen; iodine; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; In dichloromethane; toluene;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

t-butyldimethylsiyl triflate (69739-34-0) → (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester (172427-44-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: DIBALH / CH₂Cl₂ / -78 °C

3: toluene / Ambient temperature

4: 92 percent / DIBALH / CH₂Cl₂ / -78 °C

5: t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem MS / CH₂Cl₂ / -20 °C

6: SO₃*Pyr, Et₃N, DMSO / CH₂Cl₂ / 0 °C

7: toluene / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene;

DOI:10.1016/0040-4039(95)01973-L

Reference yield:

((2S,3S,4R,5R,6R)-4-Benzyloxy-3-hydroxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester → (E)-3-{(2S,3S)-3-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-acrylic acid methyl ester (172427-44-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 2,6-lutidine / CH₂Cl₂ / Ambient temperature

2: DIBALH / CH₂Cl₂ / -78 °C

3: toluene / Ambient temperature

4: 92 percent / DIBALH / CH₂Cl₂ / -78 °C

5: t-BuOOH, (+)-DET, Ti(Oi-Pr)4, 4 Angstroem MS / CH₂Cl₂ / -20 °C

6: SO₃*Pyr, Et₃N, DMSO / CH₂Cl₂ / 0 °C

7: toluene / Ambient temperature

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; pyridine-SO₃ complex; diethyl (2R,3R)-tartrate; 4 Angstroem MS; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In dichloromethane; toluene;

DOI:10.1016/0040-4039(95)01973-L

upstream raw materials:

methyl (triphenylphosphoranylidene)acetate

t-butyldimethylsiyl triflate

((2S,3S,4S,5R,6R)-3-Allyloxy-4-benzyloxy-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl)-acetic acid ethyl ester

(E)-4-[(2S,3S,4S,5R,6R)-4-Benzyloxy-3-(tert-butyl-dimethyl-silanyloxy)-5-methoxy-6-methoxymethyl-tetrahydro-pyran-2-yl]-but-2-en-1-ol

Downstream raw materials:

(2R,3R,4S,4aS,6S,7S,8aS)-4,7-Bis-benzyloxy-6-[(E)-3-((2R,3R,4S,4aS,8aS)-4-benzyloxy-3-methoxymethoxy-octahydro-pyrano[3,2-b]pyran-2-yl)-propenyl]-3-methoxy-2-methoxymethyl-octahydro-pyrano[3,2-b]pyran

C₄₄H₆₄O₁₁Si

((2S,3S,4aS,6R,7R,8S,8aS)-8-Benzyloxy-2-ethynyl-7-methoxy-6-methoxymethyl-octahydro-pyrano[3,2-b]pyran-3-yloxy)-tert-butyl-dimethyl-silane

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