(3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran

Base Information

• Chemical Name: (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran
• CAS No.: 365212-81-3
• Molecular Formula: C₃₂H₄₄O₇
• Molecular Weight: 540.697
• Mol file: 365212-81-3.mol

Synonyms:(3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran

Chemical Property of (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran

There total 14 articles about (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran 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: 78.0%

allyl bromide (106-95-6) + (3R,4aR,6S,8R,8aS)-6-(3-Benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-ol (884004-75-5) → (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran (365212-81-3)

Guidance literature:

With tetra-(n-butyl)ammonium iodide; sodium hydride; In tetrahydrofuran; for 2h; Heating;

DOI:10.1021/ol016434w

Reference yield:

4-benzyloxybutanal (5470-84-8) → (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran (365212-81-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 4 Angstroem molecular sieves / Jacobsen's tridentate Cr (III) catalyst / acetone / 52 h / 20 °C

1.2: TFA / CH₂Cl₂; acetone / 1 h / 0 °C

2.1: CeCl₃*7H₂O / ethanol / 0.33 h / 20 °C

2.2: NaBH₄ / ethanol / 2 h / -60 - 20 °C

3.1: NaH / dimethylformamide / 0.5 h / 0 °C

3.2: 97 percent / dimethylformamide / 4 h / 20 °C

4.1: dimethyldioxirane / CH₂Cl₂; acetone / -60 - 20 °C

4.2: 65 percent / tetrahydrofuran / 0 - 20 °C

5.1: 78 percent / i-Pr₂NEt; DMAP / CH₂Cl₂ / 50 h / 20 °C

6.1: TiCl₄; TMEDA; Zn / CH₂Br₂; PbCl₂ / tetrahydrofuran; CH₂Cl₂ / 2 h / Heating

6.2: 65 percent / RuCl₂(benzylidene)(PCy₃)(Mes₂C₃H₅N₂) / benzene / 16 h / 20 °C

7.1: 92 percent / m-CPBA / -60 - 20 °C

8.1: 78 percent / NaH; (C₄H₉)4NI / tetrahydrofuran / 2 h / Heating

With dmap; cerium(III) chloride; N,N,N,N,-tetramethylethylenediamine; 4 A molecular sieve; 3,3-dimethyldioxirane; titanium tetrachloride; tetra-(n-butyl)ammonium iodide; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; (1R,2R)-(-)-[1,2-cyclohexanediamine-N,N’-bis(3,5-di-tertbutylsalicylidine)]chromium(III) chloride; lead(II) chloride; 1,1-dibromomethane; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; acetone;

DOI:10.1021/ol016434w

Reference yield:

(2S,4R)-2-(3-Benzyloxy-propyl)-4-(4-methoxy-benzyloxy)-5-methyl-3,4-dihydro-2H-pyran (365212-78-8) → (3R,4aR,6S,8R,8aS)-3-Allyloxy-6-(3-benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran (365212-81-3)

Guidance literature:

Multi-step reaction with 7 steps

1: dimethyldioxirane / CH₂Cl₂; acetone / 0.5 h / -65 - 20 °C

2: 6.5 g / diethyl ether / 0.5 h / -65 - 20 °C

3: 85 percent / (i-Pr)2NEt

4: TiCl₄; TMEDA; Zn / PbCl₂ / CH₂Cl₂

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

6: 92 percent / m-CPBA

7: 78 percent / NaH / tetrahydrofuran

With N,N,N,N,-tetramethylethylenediamine; 3,3-dimethyldioxirane; titanium tetrachloride; sodium hydride; N-ethyl-N,N-diisopropylamine; 3-chloro-benzenecarboperoxoic acid; zinc; tricyclohexylphosphine[1,3-bis(2,4,6-trimethylphenyl)-4,5-dihydroimidazol-2-ylidine][benzylidene]ruthenium(II) dichloride; lead(II) chloride; In tetrahydrofuran; diethyl ether; dichloromethane; acetone; benzene;

DOI:10.1002/chem.200500993

upstream raw materials:

allyl bromide

(3R,4aR,6S,8R,8aS)-6-(3-Benzyloxy-propyl)-2-methoxy-8-(4-methoxy-benzyloxy)-2,8a-dimethyl-octahydro-pyrano[3,2-b]pyran-3-ol

p-methoxybenzyl chloride

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

Downstream raw materials:

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

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

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

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