{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol

Base Information

• Chemical Name: {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol
• CAS No.: 221380-91-2
• Molecular Formula: C₃₉H₅₆O₆Si₂
• Molecular Weight: 677.041

Synonyms:{(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol

Chemical Property of {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Useful:

Technology Process of {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol

There total 8 articles about {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-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: 89.0%

(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-but-2-en-1-ol (221380-90-1) → {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol (221380-91-2)

Guidance literature:

With titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; In 2,2,4-trimethylpentane; dichloromethane; at -25 ℃; for 19h;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

benzyl bromide (100-39-0) → {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol (221380-91-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

2: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

3: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

4: benzene / 17 h / 25 °C

5: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

6: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutylammomium bromide; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; In 2,2,4-trimethylpentane; dichloromethane; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

Reference yield:

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol (122821-81-2) → {(2S,3S)-3-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-ylmethyl]-oxiranyl}-methanol (221380-91-2)

Guidance literature:

Multi-step reaction with 7 steps

1: imidazole / CH₂Cl₂ / 1 h / 0 °C

2: 1.) nBu₂SnO, 2.) nBu₄NBr / 1.) MeOH, 60 deg C, 1 h, 2.) C₆H₆, 80 deg C, 5 h

3: 95 percent / 2,6-lutidine / CH₂Cl₂ / 4 h / 0 °C

4: 1.) O₃, 2.) PPh₃ / 1.) CH₂Cl₂, -78 deg C, 2 h, 2.) CH₂Cl₂, 25 deg C, 18 h

5: benzene / 17 h / 25 °C

6: 100 percent / DIBAL / CH₂Cl₂ / 3 h / -78 °C

7: 89 percent / (+)-DET, Ti(iPrO)4, t-BuOOH, 4 Angstroem molecular sieves / CH₂Cl₂; 2,2,4-trimethyl-pentane / 19 h / -25 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; tert.-butylhydroperoxide; diethyl (2R,3R)-tartrate; 4 A molecular sieve; tetrabutylammomium bromide; diisobutylaluminium hydride; di(n-butyl)tin oxide; ozone; triphenylphosphine; In 2,2,4-trimethylpentane; dichloromethane; benzene;

DOI:10.1002/(SICI)1521-3765(19990201)5:2<628::AID-CHEM628>3.0.CO;2-E

upstream raw materials:

(E)-4-[(2R,3S,4S,6S)-4-Benzyloxy-6-(tert-butyl-diphenyl-silanyloxymethyl)-3-triethylsilanyloxy-tetrahydro-pyran-2-yl]-but-2-en-1-ol

benzyl bromide

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

2,6-Anhydro-1-O-(tert-butyldiphenylsilyl)-3,7,8,9-tetradeoxy-4,5-O-isopropylidene-D-altro-non-8-enitol

Downstream raw materials:

5-benzyloxy-2-{3-[5-(tert-butyl-dimethyl-silanyloxy)-2-phenyl-[1,3]dioxan-4-yl]-propenyl}-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracene

C₅₁H₈₄O₉Si₃

(2R,4S,5R)-4-((Z)-3-{(2R,4aR,5S,7R,8aR,9aS,10aS)-5-Benzyloxy-7-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-3,3-bis-ethylsulfanyl-decahydro-1,8,10-trioxa-anthracen-2-yl}-allyl)-2-phenyl-[1,3]dioxan-5-ol

C₄₉H₈₂O₈Si₃

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