[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Base Information

Chemical Name:[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester
CAS No.:319922-50-4
Molecular Formula:C₃₃H₅₆O₁₀Si₂
Molecular Weight:668.973
Hs Code.:

[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Synonyms:[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

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Chemical Property of [6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

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Technology Process of [6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

There total 18 articles about [6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester 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:

: 228419-57-6
(2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-hex-5-en-3-ol

: 319922-50-4
[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 9 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

7: 84 percent / NMO; OsO₄ / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH₇ buffer

8: NaIO₄ / tetrahydrofuran / 2 h / 20 °C / pH₇ buffer

9: DBU; LiCl / acetonitrile / 23 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; potassium osmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; 5: Swern oxidation / 9: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001236o

Reference yield:

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

: 319922-50-4
[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 10 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

8.1: 84 percent / NMO; OsO₄ / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH₇ buffer

9.1: NaIO₄ / tetrahydrofuran / 2 h / 20 °C / pH₇ buffer

10.1: DBU; LiCl / acetonitrile / 23 h / 20 °C

With pyridine; 2,6-dimethylpyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; magnesium bromide; potassium osmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; 6.1: Swern oxidation / 10.1: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001236o

Reference yield:

: 228419-66-7
(2R,3R,4R)-4-(tert-butyldimethylsilanyloxy)-1-(4-methoxy-benzyloxy)-2,5-dimethyl-3-triethylsilanyloxy-hex-5-en

: 319922-50-4
[6-[1'-(tert-butyldimethylsilanyloxy)-1'-(4-methyl-2-oxo-[1,3]-dioxolan-4-yl)-methyl]-4-triethylsilanyloxy-3-(4-methoxy-phenoxy)-5-methyl-tetrahydro-pyran-2-yl]-acetic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

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

2: 99 percent / pyridine / CH₂Cl₂ / 1.5 h / -78 - 0 °C

3: 90 percent / DDQ / CH₂Cl₂ / 1 h / pH 7 / pH 7 buffer

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

5: 4.92 g / BF₃*Et₂O / CH₂Cl₂ / -78 - -10 °C

6: 84 percent / NMO; OsO₄ / tetrahydrofuran; acetone; toluene / 48 h / 20 °C / pH₇ buffer

7: NaIO₄ / tetrahydrofuran / 2 h / 20 °C / pH₇ buffer

8: DBU; LiCl / acetonitrile / 23 h / 20 °C

With pyridine; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; oxalyl dichloride; methanesulfonamide; boron trifluoride diethyl etherate; potassium carbonate; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1,4-bis(9-O-dihydroquinidine)phthalazine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium chloride; potassium osmate(VI); potassium hexacyanoferrate(III); In tetrahydrofuran; dichloromethane; water; acetone; toluene; acetonitrile; tert-butyl alcohol; 4: Swern oxidation / 8: Horner-Wadsworth-Emmons reaction;
DOI:10.1021/jo001236o