4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

Base Information

Chemical Name:4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one
CAS No.:228419-61-2
Molecular Formula:C₃₁H₅₄O₈Si₂
Molecular Weight:610.936
Hs Code.:

4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

Synonyms:4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

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Chemical Property of 4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

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Technology Process of 4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

There total 10 articles about 4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-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: 93.0%

: 228419-56-5
(Z)-γ-(4-methoxy-phenoxy)allyltributylstannane

: 228419-60-1
(1S,2R,3S)-4-(tert-butyldimethylsilanyloxy)-2-methyl-4-(4-methyl-2-oxo-[1,3]dioxolan-4-yl)-3-triethylsilanyloxy-butyraldehyde

: 228419-61-2
4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 - -10 ℃;
DOI:10.1016/S0040-4039(99)00464-5

Reference yield:

: 228419-55-4
(Z)-γ-(tert-butyldimethylsilanyloxy)methallyltributylstannane

: 228419-61-2
4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

Guidance literature:: Multi-step reaction with 7 steps

1.1: MgBr₂*Et₂O / CH₂Cl₂ / 0.5 h / -25 °C

1.2: 93 percent / CH₂Cl₂ / -25 - 23 °C

2.1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.83 h / -78 - -50 °C

3.1: (DHQD)2-phal; methanesulfonamide; K₂CO₃ / K₃Fe(CN)6; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 21 h / 0 °C

4.1: 99 percent / pyridine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

5.1: 90 percent / DDQ / CH₂Cl₂ / 1 h / pH 7 / pH 7 buffer

6.1: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

7.1: 4.92 g / BF₃*Et₂O / CH₂Cl₂ / -78 - -10 °C

With pyridine; 2,6-dimethylpyridine; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; magnesium bromide; potassium osmate(VI); potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; 6.1: Swern oxidation;
DOI:10.1021/jo001236o

Reference yield:

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 228419-61-2
4-[(1S,2R,3R,4R,5R)-1-(tert-butyldimethylsilanyloxy)-4-hydroxy-5-(4-methoxy-phenoxy)-3-methyl-2-triethylsilanyloxy-hept-6-enyl]4-methyl-[1,3]-dioxolan-2-one

Guidance literature:: Multi-step reaction with 6 steps

1: 92 percent / 2,6-lutidine / CH₂Cl₂ / 0.83 h / -78 - -50 °C

2: (DHQD)2-phal; methanesulfonamide; K₂CO₃ / K₃Fe(CN)6; K₂OsO₄*2H₂O / 2-methyl-propan-2-ol; H₂O / 21 h / 0 °C

3: 99 percent / pyridine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

4: 90 percent / DDQ / CH₂Cl₂ / 1 h / pH 7 / pH 7 buffer

5: (COCl)2; DMSO / CH₂Cl₂ / 0.17 h / -78 °C

6: 4.92 g / BF₃*Et₂O / CH₂Cl₂ / -78 - -10 °C

With pyridine; 2,6-dimethylpyridine; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; potassium osmate(VI); potassium hexacyanoferrate(III); In dichloromethane; water; tert-butyl alcohol; 5: Swern oxidation;
DOI:10.1021/jo001236o