[(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Base Information

• Chemical Name: [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane
• CAS No.: 256342-05-9
• Molecular Formula: C₄₂H₆₄O₁₀Si
• Molecular Weight: 757.05

Synonyms:[(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Chemical Property of [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

There total 24 articles about [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane 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%

triisopropylsilyl trifluoromethanesulfonate (80522-42-5) + (2R,3R,4S,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol (256342-26-4) → [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (256342-05-9)

Guidance literature:

With 2,6-dimethylpyridine; In dichloromethane; at 0 - 25 ℃; for 1h;

DOI:10.1002/(SICI)1521-3773(19991115)38:22<3340::AID-ANIE3340>3.0.CO;2-2 DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

Trifluoro-methanesulfonate2-[(1R,2R,3S)-2,3-bis-allyloxy-1-benzoyloxy-4-(tert-butyl-diphenyl-silanyloxy)-butyl]-3-methyl-thiazol-3-ium; → [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (256342-05-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: NaBH₄ / methanol / 0.5 h / 0 °C

1.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

2.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

3.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

4.1: nBu₂SnO / methanol / 3 h / Heating

4.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

4.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

5.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

6.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

7.1: NaH / dimethylformamide / 0.08 h / 0 °C

7.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

8.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

9.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

With 2,6-dimethylpyridine; methanol; sodium hydroxide; sodium tetrahydroborate; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; 1.1: Reduction / 1.2: Ring cleavage / 2.1: Cyclization / 3.1: Addition / 4.1: Cyclization / 4.2: Ring cleavage / 4.3: Methanolysis / 5.1: Methylation / 6.1: Debenzoylation / 7.1: Metallation / 7.2: Etherification / 8.1: Oxidation / 9.1: Etherification;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

Reference yield:

Benzoic acid (1R,2R,3S)-2,3-bis-allyloxy-4-(tert-butyl-diphenyl-silanyloxy)-1-thiazol-2-yl-butyl ester (306726-12-5) → [(2R,3R,4R,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (256342-05-9)

Guidance literature:

Multi-step reaction with 10 steps

1.1: molecular sieves 4 Angstroem / acetonitrile / 0.25 h / 25 °C

2.1: NaBH₄ / methanol / 0.5 h / 0 °C

2.2: H₂O; CuCl₂; CuO / acetonitrile / 2 h / 25 °C

3.1: 10.97 g / TBAF; AcOH / 2 h / 25 °C

4.1: 85 percent / DBU / CH₂Cl₂ / 0.5 h / 0 °C

5.1: nBu₂SnO / methanol / 3 h / Heating

5.2: TMSOTf / CH₂Cl₂ / 12 h / 0 - 25 °C

5.3: 10.82 g / PPTS; MeOH / 1 h / 25 °C

6.1: 87 percent / NaH / dimethylformamide / 1 h / 0 - 25 °C

7.1: 95 percent / NaOH; MeOH / diethyl ether / 1 h / 25 °C

8.1: NaH / dimethylformamide / 0.08 h / 0 °C

8.2: 90 percent / nBu₄NI / dimethylformamide / 4 h / 0 - 25 °C

9.1: 91 percent / DDQ; H₂O / CH₂Cl₂ / 1 h / 0 - 25 °C

10.1: 97 percent / 2,6-lutidine / CH₂Cl₂ / 1 h / 0 - 25 °C

With 2,6-dimethylpyridine; methanol; sodium hydroxide; sodium tetrahydroborate; 4 A molecular sieve; tetrabutyl ammonium fluoride; water; sodium hydride; di(n-butyl)tin oxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Methylation / 2.1: Reduction / 2.2: Ring cleavage / 3.1: Cyclization / 4.1: Addition / 5.1: Cyclization / 5.2: Ring cleavage / 5.3: Methanolysis / 6.1: Methylation / 7.1: Debenzoylation / 8.1: Metallation / 8.2: Etherification / 9.1: Oxidation / 10.1: Etherification;

DOI:10.1002/1521-3765(20000901)6:17<3116::AID-CHEM3116>3.0.CO;2-8

upstream raw materials:

triisopropylsilyl trifluoromethanesulfonate

(2R,3R,4S,5S,6S)-4-Benzyloxy-6-((2S,3R,4R,5S)-4,5-bis-allyloxy-3-benzyloxy-tetrahydro-pyran-2-yloxy)-5-methoxy-2-methoxymethyl-tetrahydro-pyran-3-ol

benzyl bromide

phenyl 2,3-di-O-isopropylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

(3S,4R,5R,6S)-5-Benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-3,4-diol

Chloro-acetic acid (3S,4R,5R,6S)-5-benzyloxy-6-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-4-hydroxy-tetrahydro-pyran-3-yl ester

Chloro-acetic acid (2S,3R,4R,5S)-3-benzyloxy-2-((2S,3S,4R,5R,6R)-4-benzyloxy-3-methoxy-6-methoxymethyl-5-triisopropylsilanyloxy-tetrahydro-pyran-2-yloxy)-5-hydroxy-tetrahydro-pyran-4-yl ester

C₄₀H₄₈O₁₃

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