4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

Base Information

Chemical Name:4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole
CAS No.:1026407-02-2
Molecular Formula:C₃₀H₄₃NO₅Si
Molecular Weight:525.761
Hs Code.:

4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

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Chemical Property of 4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

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Technology Process of 4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

There total 8 articles about 4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole 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:

: 60656-87-3
benzyloxyacetoaldehyde

: 1026407-02-2
4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 8 steps

1.1: 87 percent / PPTS; MeOH / [(R,R)Cu(Ph-pybox)](SbF₆)2 / CH₂Cl₂ / 16 h / -78 °C

2.1: 99 percent / K₂CO₃; MeOH / 17 h / 20 °C

3.1: DIBAL / CH₂Cl₂ / -50 °C

3.2: pyridine; DMAP / CH₂Cl₂ / -78 - 0 °C

4.1: 97 percent / BF₃*OEt₂; TMSOTf; 4 Angstroem mol. sieves / acetonitrile / 1.5 h / -30 - -18 °C

5.1: LiCl; DBU / acetonitrile; CH₂Cl₂ / 3 h / 20 °C

6.1: Et₃N / diethyl ether / 0 - 20 °C

7.1: Jacobsen catalyst; 4 Angstroem mol. sieves / acetone / 3 h

7.2: 38 h

With methanol; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; pyridinium p-toluenesulfonate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; [(R,R)Cu(Ph-pybox)](SbF₆)2; In diethyl ether; dichloromethane; acetone; acetonitrile; 1.1: Evans aldol reaction / 8.1: Jacobsen hetero Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)00754-8

Reference yield:

: 570389-08-1
(R)-(3-benzyloxy-2-hydroxypropyl)-2,2-dimethyl-1,3-dioxin-4-one

: 1026407-02-2
4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 7 steps

1.1: 99 percent / K₂CO₃; MeOH / 17 h / 20 °C

2.1: DIBAL / CH₂Cl₂ / -50 °C

2.2: pyridine; DMAP / CH₂Cl₂ / -78 - 0 °C

3.1: 97 percent / BF₃*OEt₂; TMSOTf; 4 Angstroem mol. sieves / acetonitrile / 1.5 h / -30 - -18 °C

4.1: LiCl; DBU / acetonitrile; CH₂Cl₂ / 3 h / 20 °C

5.1: Et₃N / diethyl ether / 0 - 20 °C

6.1: Jacobsen catalyst; 4 Angstroem mol. sieves / acetone / 3 h

6.2: 38 h

With methanol; (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In diethyl ether; dichloromethane; acetone; acetonitrile; 7.1: Jacobsen hetero Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)00754-8

Reference yield:

: 570389-10-5
(R)-6-Benzyloxymethyl-dihydro-pyran-2,4-dione

: 1026407-02-2
4-[(2R,6R)-6-((2R,6R)-6-Benzyloxymethyl-4-methylene-tetrahydro-pyran-2-ylmethyl)-4-triethylsilanyloxy-3,6-dihydro-2H-pyran-2-yl]-2-methyl-oxazole

Guidance literature:: Multi-step reaction with 6 steps

1.1: DIBAL / CH₂Cl₂ / -50 °C

1.2: pyridine; DMAP / CH₂Cl₂ / -78 - 0 °C

2.1: 97 percent / BF₃*OEt₂; TMSOTf; 4 Angstroem mol. sieves / acetonitrile / 1.5 h / -30 - -18 °C

3.1: LiCl; DBU / acetonitrile; CH₂Cl₂ / 3 h / 20 °C

4.1: Et₃N / diethyl ether / 0 - 20 °C

5.1: Jacobsen catalyst; 4 Angstroem mol. sieves / acetone / 3 h

5.2: 38 h

With (S,S)-chloro[2,2'-[1,2-cyclohexanediylbis(nitrilomethylidyne)]bis-[4,6-bis(1,1-dimethylethyl)phenolato]]^(2-)-N,N',O,O'-manganese; trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; boron trifluoride diethyl etherate; diisobutylaluminium hydride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; lithium chloride; In diethyl ether; dichloromethane; acetone; acetonitrile; 6.1: Jacobsen hetero Diels-Alder reaction;
DOI:10.1016/S0040-4039(03)00754-8