2H-Pyran-2-carboxylic acid, 6-[(2S)-3-[(2R,4S,6S)-6-(cyanomethyl)-4-[[(1,1-dimethylethyl)diphenylsil yl]oxy]tetrahydro-2H-pyran-2-yl]-2-methoxypropyl]-5,6-dihydro-5-methyl-, 1-methylethyl ester, (2S,5S,6R)-

Base Information

• Chemical Name: 2H-Pyran-2-carboxylic acid, 6-[(2S)-3-[(2R,4S,6S)-6-(cyanomethyl)-4-[[(1,1-dimethylethyl)diphenylsil yl]oxy]tetrahydro-2H-pyran-2-yl]-2-methoxypropyl]-5,6-dihydro-5-methyl-, 1-methylethyl ester, (2S,5S,6R)-
• CAS No.: 850404-96-5
• Molecular Formula: C37H51NO6Si
• Molecular Weight: 633.901
• Mol file: 850404-96-5.mol

Synonyms:

Chemical Property of 2H-Pyran-2-carboxylic acid, 6-[(2S)-3-[(2R,4S,6S)-6-(cyanomethyl)-4-[[(1,1-dimethylethyl)diphenylsil yl]oxy]tetrahydro-2H-pyran-2-yl]-2-methoxypropyl]-5,6-dihydro-5-methyl-, 1-methylethyl ester, (2S,5S,6R)-

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2H-Pyran-2-carboxylic acid, 6-[(2S)-3-[(2R,4S,6S)-6-(cyanomethyl)-4-[[(1,1-dimethylethyl)diphenylsil yl]oxy]tetrahydro-2H-pyran-2-yl]-2-methoxypropyl]-5,6-dihydro-5-methyl-, 1-methylethyl ester, (2S,5S,6R)-

There total 14 articles about 2H-Pyran-2-carboxylic acid, 6-[(2S)-3-[(2R,4S,6S)-6-(cyanomethyl)-4-[[(1,1-dimethylethyl)diphenylsil yl]oxy]tetrahydro-2H-pyran-2-yl]-2-methoxypropyl]-5,6-dihydro-5-methyl-, 1-methylethyl ester, (2S,5S,6R)- 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: 73.0%

(E)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hydroxy-hex-4-enoic acid isopropyl ester (850404-86-3) + [4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile (850404-87-4) → (2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester (850404-96-5) + (2R,5S,6R)-6-{(S)-3-[(2R,4S,6S)-4-(tert-Butyl-diphenyl-silanyloxy)-6-cyanomethyl-tetrahydro-pyran-2-yl]-2-methoxy-propyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -50 ℃; for 12h;

DOI:10.1002/anie.200462408

Reference yield: 73.0%

[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile (850404-87-4) + (2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester (1027201-42-8) → (2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester (850404-96-5) + (2S,5S,6S)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -50 ℃; for 12h;

DOI:10.1021/jo0610412

Reference yield:

2,4,6-Trimethyl-benzenesulfonic acid (2S,3S)-3-(dimethyl-phenyl-silanyl)-2-hydroxy-pent-4-enyl ester (850405-01-5) → (2S,5S,6R)-6-{(2S)-3-[(2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-cyanomethyltetrahydro-2H-pyran-2-yl]-2-methoxypropyl}-5-methyl-5,6-dihydro-2H-pyran-2-carboxylic acid isopropyl ester (850404-96-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 92 percent / pyridine / tetrahydrofuran / 12 h

2.1: 80 percent / TfOH / CH₂Cl₂ / 12 h / -78 °C

3.1: 87 percent / dimethylformamide / 60 h / 60 °C

4.1: mercury trifluoroacetate / tetrahydrofuran / 18 h

4.2: 76 percent / NaBH₄; NaOH / tetrahydrofuran

5.1: 95 percent / imidazole / dimethylformamide / 72 h

6.1: 90 percent / BCl₃ / hexane; CH₂Cl₂ / 20 h / -78 °C

7.1: 85 percent / pyridinium chlorochromate; molecular sieves / CH₂Cl₂ / 2 h

8.1: 73 percent / trimethylsilyl triflate / CH₂Cl₂ / 12 h / -50 °C

With pyridine; 1H-imidazole; molecular sieve; trifluorormethanesulfonic acid; trimethylsilyl trifluoromethanesulfonate; mercury(II) trifluoroacetate; boron trichloride; pyridinium chlorochromate; In tetrahydrofuran; hexane; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jo0610412

upstream raw materials:

(E)-(2R,3S)-3-(Dimethyl-phenyl-silanyl)-2-hydroxy-hex-4-enoic acid isopropyl ester

[4-(tert-butyldiphenylsilanyloxy)-6-(2-methoxy-4-oxobutyl)-tetrahydro-2H-pyran-2-yl]acetonitrile

(2R,3S,4E)-3-(dimethylphenylsilanyl)-2-hydroxyhex-4-enoic acid isopropyl ester

(2S,3S)-3-(Dimethyl-phenyl-silanyl)-pent-4-ene-1,2-diol

Downstream raw materials:

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-formyl-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-2-methoxy-3-((2R,3S,6S)-3-methyl-6-(oxoethyl)tetrahydro-2H-pyran-2-yl)propyl]tetrahydro-2H-pyran-2-yl}acetonitrile

(1R,3S,5R,7R,9R,13R,15S,18S)-7-(tert-Butyl-diphenyl-silanyloxy)-3-methoxy-18-methyl-13-((E)-4-methyl-pent-1-enyl)-12,19,20-trioxa-tricyclo[13.3.1.1^5,9]icosan-11-ol

{(2S,4S,6R)-4-(tert-butyldiphenylsilanyloxy)-6-[(2S)-3-((2R,3S,6S)-6-((2R,3E)-2-hydroxy-6-methylhept-3-enyl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl]tetrahydro-2H-pyran-2-yl}acetonitrile