[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Base Information

• Chemical Name: [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane
• CAS No.: 474248-58-3
• Molecular Formula: C₄₆H₆₂O₅SSi
• Molecular Weight: 755.147

Synonyms:[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Chemical Property of [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Chemical Property:

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Technology Process of [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

There total 1 articles about [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-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: 100.0%

diphenyldisulfane (882-33-7) + (R)-3-Benzyloxy-3-((2S,3R,5S,6R)-5-benzyloxy-6-benzyloxymethyl-2-methyl-3-triisopropylsilanyloxy-tetrahydro-pyran-2-yl)-propan-1-ol → [(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (474248-58-3)

Guidance literature:

With tributylphosphine; In pyridine; at 20 ℃; for 24h;

DOI:10.1021/ol026529d

Reference yield:

[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (474248-58-3) → [(2S,3R,5S,6R)-5-Benzyloxy-2-((R)-1-benzyloxy-3-chloro-3-phenylsulfanyl-propyl)-6-benzyloxymethyl-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane

Guidance literature:

With N-chloro-succinimide; In tetrachloromethane; at 20 ℃; for 0.333333h;

DOI:10.1021/ol026529d

Reference yield:

[(2S,3R,5S,6R)-5-Benzyloxy-6-benzyloxymethyl-2-((R)-1-benzyloxy-3-phenylsulfanyl-propyl)-2-methyl-tetrahydro-pyran-3-yloxy]-triisopropyl-silane (474248-58-3) → C58H66O9

Guidance literature:

Multi-step reaction with 7 steps

1.1: N-chlorosuccinimide / CCl₄ / 0.33 h / 20 °C

2.1: 212.1 mg / silver triflate; 2,6-di-tert-butyl-4-methylpyridine; molecular sieves 4 Angstroem / CH₂Cl₂ / -60 °C

3.1: 87 percent / tetra-n-butylammonium fluoride / tetrahydrofuran / 4.5 h / 35 °C

4.1: 100 percent / 4-methylmorpholine / CH₂Cl₂ / 48 h

5.1: tri-n-butylstannane; azobis(isobutyronitrile) / toluene / 7 h / 80 °C

5.2: DIBAL / CH₂Cl₂ / 1.5 h / -90 °C

6.1: 71.7 mg / sodium bis(trimethylsilyl)amide / tetrahydrofuran / 0.17 h / 0 °C

7.1: 100 percent / (PCy₃)2Cl₂Ru=CHPh / CH₂Cl₂ / 3 h / Heating

With 4-methyl-morpholine; N-chloro-succinimide; 2,6-di-tert-butyl-4-methylpyridine; 2,2'-azobis(isobutyronitrile); 4 A molecular sieve; tetrabutyl ammonium fluoride; tri-n-butyl-tin hydride; silver trifluoromethanesulfonate; sodium hexamethyldisilazane; Grubbs catalyst first generation; In tetrahydrofuran; tetrachloromethane; dichloromethane; toluene; 6.1: Wittig olefination;

DOI:10.1021/ol026529d

upstream raw materials:

diphenyldisulfane

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