(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

Base Information

Chemical Name:(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman
CAS No.:850816-11-4
Molecular Formula:C₆₈H₇₀O₇
Molecular Weight:999.3
Hs Code.:

Synonyms:(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

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Chemical Property of (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

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Technology Process of (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

There total 18 articles about (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman 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: 65.0%

: 850816-18-1
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-ol

: 850816-11-4
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

Guidance literature:: (2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman-3-ol; With dmap; phenyl trichloroformate; In acetonitrile; at 70 ℃; for 6h;

With tri-n-butyl-tin hydride; 2,2'-azobis(isobutyronitrile); In toluene; at 110 ℃; for 8h;
DOI:10.1021/ja042727j

Reference yield:

: 850816-15-8
(2R,3S)-2-(4-benzyloxyphenyl)-7-benzyloxychroman-3-yl formate

: 850816-11-4
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

Guidance literature:: Multi-step reaction with 8 steps

1.1: 98 percent / K₂CO₃ / methanol; tetrahydrofuran / 2 h / 20 °C

2.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

3.1: 78 percent / LiBr; L-selectride / tetrahydrofuran / -78 - 20 °C

4.1: 93 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: 79 percent / DDQ; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 0 °C

6.1: 78 percent / TMSOTf / tetrahydrofuran / -35 - -5 °C / pH 7

7.1: 100 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 °C

8.1: 4-N,N-dimethylaminopyridine; phenyl trichloroformate / acetonitrile / 6 h / 70 °C

8.2: 65 percent / SnBu₃H / AIBN / toluene / 8 h / 110 °C

With dmap; trimethylsilyl trifluoromethanesulfonate; phenyl trichloroformate; L-Selectride; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; dmap; In tetrahydrofuran; methanol; dichloromethane; acetonitrile;
DOI:10.1021/ja042727j

Reference yield:

: (E)-1-(4-benzyloxyphenyl)-3-(4-benzyloxy-2-hydroxyphenyl)propene

: 850816-11-4
(2R,3R,4R)-2-(4-benzyloxyphenyl)-7-benzyloxy-4-(2,4,6-tribenzyloxy-3-(dodecanoyl)phenyl)chroman

Guidance literature:: Multi-step reaction with 13 steps

1.1: 100 percent / imidazole / dimethylformamide / 20 °C

2.1: 84 percent / AD-Mix α; methanesulfonamide / 2-methyl-propan-2-ol; H2O / 20 °C

3.1: 92 percent / pyridinium p-toluenesulfonate / CH₂Cl₂ / 1 h / 20 °C

4.1: 100 percent / tert-n-butylammonium fluoride / tetrahydrofuran / 1 h / 20 °C

5.1: 89 percent / triethyl orthoformate; pyridinium p-toluenesulfonate / 1,2-dichloro-ethane / 2 h / 60 °C

6.1: 98 percent / K₂CO₃ / methanol; tetrahydrofuran / 2 h / 20 °C

7.1: 94 percent / Dess-Martin periodinane / CH₂Cl₂ / 2 h / 20 °C

8.1: 78 percent / LiBr; L-selectride / tetrahydrofuran / -78 - 20 °C

9.1: 93 percent / 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 2 h / 20 °C

10.1: 79 percent / DDQ; 4-N,N-dimethylaminopyridine / CH₂Cl₂ / 0.25 h / 0 °C

11.1: 78 percent / TMSOTf / tetrahydrofuran / -35 - -5 °C / pH 7

12.1: 100 percent / K₂CO₃ / tetrahydrofuran; methanol / 20 °C

13.1: 4-N,N-dimethylaminopyridine; phenyl trichloroformate / acetonitrile / 6 h / 70 °C

13.2: 65 percent / SnBu₃H / AIBN / toluene / 8 h / 110 °C

With 1H-imidazole; dmap; AD-mix-α; methanesulfonamide; trimethylsilyl trifluoromethanesulfonate; phenyl trichloroformate; tetrabutyl ammonium fluoride; pyridinium p-toluenesulfonate; L-Selectride; potassium carbonate; Dess-Martin periodane; orthoformic acid triethyl ester; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium bromide; dmap; In tetrahydrofuran; methanol; dichloromethane; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; tert-butyl alcohol; 2.1: Sharpless asymmetric dihydroxylation;
DOI:10.1021/ja042727j