(2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

Base Information

• Chemical Name: (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one
• CAS No.: 365212-83-5
• Molecular Formula: C₂₆H₄₀O₅Si
• Molecular Weight: 460.686
• Mol file: 365212-83-5.mol

Synonyms:(2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

Chemical Property of (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one

There total 14 articles about (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one 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%

trimethylsilyl trifluoromethanesulfonate (27607-77-8) + (2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one (365212-90-4) → (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one (365212-83-5)

Guidance literature:

With triethylamine; In N,N-dimethyl-formamide;

DOI:10.1002/chem.200500993

Reference yield:

C24H30O5 → (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one (365212-83-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C

2: 85 percent / (i-Pr)2NEt

3: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂

4: PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 20 °C

5: 92 percent / m-CPBA

6: 78 percent / NaH / tetrahydrofuran

7: PPTS; pyridine / toluene / 100 °C

8: 97 percent / DDQ; H₂O / CH₂Cl₂

9: DEAD; PPh₃ / toluene

10: NaOH / tetrahydrofuran; methanol

11: 97 percent / NEt₃ / dimethylformamide

With pyridine; sodium hydroxide; N,N,N,N,-tetramethylethylenediamine; water; pyridinium p-toluenesulfonate; titanium tetrachloride; sodium hydride; triethylamine; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 9: Mitsunobu inversion;

DOI:10.1002/chem.200500993

Reference yield:

C30H40O5 → (2R,4aR,6S,8S,8aR)-2-Allyl-6-(3-benzyloxy-propyl)-2,8a-dimethyl-8-trimethylsilanyloxy-hexahydro-pyrano[3,2-b]pyran-3-one (365212-83-5)

Guidance literature:

Multi-step reaction with 8 steps

1: PhCH=RuCH{[(Mes)NCH₂CH₂N(Mes)]}(PCy₃)Cl₂ / benzene / 20 °C

2: 92 percent / m-CPBA

3: 78 percent / NaH / tetrahydrofuran

4: PPTS; pyridine / toluene / 100 °C

5: 97 percent / DDQ; H₂O / CH₂Cl₂

6: DEAD; PPh₃ / toluene

7: NaOH / tetrahydrofuran; methanol

8: 97 percent / NEt₃ / dimethylformamide

With pyridine; sodium hydroxide; water; pyridinium p-toluenesulfonate; sodium hydride; triethylamine; 3-chloro-benzenecarboperoxoic acid; triphenylphosphine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; diethylazodicarboxylate; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; toluene; benzene; 6: Mitsunobu inversion;

DOI:10.1002/chem.200500993

upstream raw materials:

trimethylsilyl trifluoromethanesulfonate

(2R,4aR,6S,8S,8aS)-2-Allyl-6-(3-benzyloxy-propyl)-8-hydroxy-2,8a-dimethyl-hexahydro-pyrano[3,2-b]pyran-3-one

(2S,4R)-2-(3-Benzyloxy-propyl)-5-methyl-3,4-dihydro-2H-pyran-4-ol

(2S,4R)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-5-methyl-3,4-dihydro-2H-pyran

Downstream raw materials:

C₂₈H₄₄O₅Si

[2-(3-benzyloxy-propyl)-4a,10a-dimethyl-3,4,4a,5,8a,9,9a,10a-octahydro-2H-1,8,10-trioxa-anthracen-4-yloxy]-trimethyl-silane

C₂₆H₄₀O₆Si

C₂₆H₄₂O₆Si