tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane

Base Information

• Chemical Name: tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane
• CAS No.: 585526-33-6
• Molecular Formula: C₃₆H₅₈O₇Si
• Molecular Weight: 630.938
• Mol file: 585526-33-6.mol

Synonyms:tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane

Chemical Property of tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane

There total 14 articles about tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane 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: 95.0%

methanol (67-56-1) + (2R,3S,9S,10R)-2-(tert-Butyl-dimethyl-silanyloxy)-1,11-bis-(4-methoxy-benzyloxy)-3,9-dimethyl-10-triethylsilanyloxy-undecan-6-one (585526-32-5) → tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane (585526-33-6)

Guidance literature:

With pyridinium p-toluenesulfonate; at 20 ℃;

DOI:10.1016/S0040-4039(03)01184-5

Reference yield:

(2E)-4-[(4-methoxyphenyl)methoxy]-2-methylbut-2-en-1-ol (167687-19-6) → tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane (585526-33-6)

Guidance literature:

Multi-step reaction with 10 steps

1.1: (+)-DET; Ti(OiPr)4; tBuOOH / MS-4A / CH₂Cl₂ / -25 °C

2.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

3.1: benzene / 20 °C

4.1: 96 percent / Pd₂(dba)3*CHCl₃; n-Bu₃P; HCO₂H / triethylamine; dioxane

5.1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

6.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 20 °C

6.2: Pb(OAc)4 / toluene / 20 °C

7.1: PPh₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

7.2: n-BuLi / tetrahydrofuran / -78 - 20 °C

8.1: 91 percent / LHMDS / tetrahydrofuran / -78 - 20 °C

9.1: 99 percent / H₂ / Pd/C / ethyl acetate / 20 °C

10.1: 95 percent / PPTS / 20 °C

With 1H-imidazole; titanium(IV) isopropylate; tert.-butylhydroperoxide; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; oxalyl dichloride; diethyl (2R,3R)-tartrate; tributylphosphine; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; triethylamine; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene; 3.1: Wittig reaction;

DOI:10.1016/S0040-4039(03)01184-5

Reference yield:

[3-(4-methoxybenzyloxymethyl)-2-methyloxiranyl]methanol (167687-20-9) → tert-Butyl-{(1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butoxy}-dimethyl-silane (585526-33-6)

Guidance literature:

Multi-step reaction with 9 steps

1.1: (COCl)2; DMSO / CH₂Cl₂ / -78 °C

2.1: benzene / 20 °C

3.1: 96 percent / Pd₂(dba)3*CHCl₃; n-Bu₃P; HCO₂H / triethylamine; dioxane

4.1: 99 percent / imidazole / dimethylformamide / 0 - 20 °C

5.1: OsO₄; NMO / acetone; H₂O; 2-methyl-propan-2-ol / 20 °C

5.2: Pb(OAc)4 / toluene / 20 °C

6.1: PPh₃; Et₃N / CH₂Cl₂ / 0 - 20 °C

6.2: n-BuLi / tetrahydrofuran / -78 - 20 °C

7.1: 91 percent / LHMDS / tetrahydrofuran / -78 - 20 °C

8.1: 99 percent / H₂ / Pd/C / ethyl acetate / 20 °C

9.1: 95 percent / PPTS / 20 °C

With 1H-imidazole; tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; osmium(VIII) oxide; formic acid; N-methyl-2-indolinone; oxalyl dichloride; tributylphosphine; hydrogen; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; triphenylphosphine; lithium hexamethyldisilazane; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; ethyl acetate; triethylamine; N,N-dimethyl-formamide; acetone; tert-butyl alcohol; benzene; 2.1: Wittig reaction;

DOI:10.1016/S0040-4039(03)01184-5

upstream raw materials:

methanol

(2R,3S,9S,10R)-2-(tert-Butyl-dimethyl-silanyloxy)-1,11-bis-(4-methoxy-benzyloxy)-3,9-dimethyl-10-triethylsilanyloxy-undecan-6-one

tert-butyldimethylsilyl chloride

3R-(tert-butyl-dimethyl-silanyloxy)-4-(4-methoxy-benzyloxy)-2R-methyl-butyraldehyde

Downstream raw materials:

Methanesulfonic acid (1R,2S)-1-(4-methoxy-benzyloxymethyl)-4-[(2S,5S,6R)-2-methoxy-6-(4-methoxy-benzyloxymethyl)-5-methyl-tetrahydro-pyran-2-yl]-2-methyl-butyl ester