(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal

Base Information

• Chemical Name: (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal
• CAS No.: 944740-80-1
• Molecular Formula: C₅₃H₈₀O₉Si
• Molecular Weight: 889.298
• Mol file: 944740-80-1.mol

Synonyms:(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal

Chemical Property of (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal

There total 14 articles about (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal 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: 85.0%

(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene (188786-19-8) → (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal (944740-80-1)

Guidance literature:

(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene; With pyridine; oil scarlet; ozone; In dichloromethane; at -78 ℃;

With triphenylphosphine; In dichloromethane; at 20 ℃; for 2h; Further stages.;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecane-7,9-diol (944740-72-1) → (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal (944740-80-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

2.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C

3.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH₂Cl₂ / 2 h / 20 °C

4.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 5 h / -78 °C

5.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

6.1: ozone; pyridine; Sudan III / CH₂Cl₂ / -78 °C

6.2: 85 percent / triphenylphosphine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; oil scarlet; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; 3.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one (188786-05-2) → (2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanal (944740-80-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

2.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

3.1: 88 percent / acetic acid; tetrabutylammonium fluoride / tetrahydrofuran / 40 h / 20 °C

4.1: 96 percent / 1,1,1-triacetoxy-1,1-dihydro-1,2-benziodoxol-3(1H)-one; pyridine / CH₂Cl₂ / 2 h / 20 °C

5.1: 69 percent / BF₃*OEt₂ / CH₂Cl₂ / 5 h / -78 °C

6.1: 91 percent / molecular sieves 3 Angstroem; DDQ / CH₂Cl₂ / 0.5 h / 20 °C

7.1: ozone; pyridine; Sudan III / CH₂Cl₂ / -78 °C

7.2: 85 percent / triphenylphosphine / CH₂Cl₂ / 2 h / 20 °C

With pyridine; oil scarlet; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; tetramethylammonium borohydride; Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; acetonitrile; 4.1: Dess-Martin oxidation;

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-4,6-[(4-methoxybenzylidene)dioxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecene

(2S,3R,4R,6R,8R,9S,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-9-hydroxy-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecan-7-one

(2S,3R,4R,6R,7S,8S,9R,10R,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyltridecane-7,9-diol

(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-4-[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanol

Downstream raw materials:

(2R,3S,4S,5R,6R,7R,9S,10S,11S,12S,13R)-13-[(benzyloxy)methoxy]-6-[(tert-butyldimethylsilyl)oxy]-3,5-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6,8,10,12-hexamethyl-9,11-{[(R)-2,4,6-trimethylbenzylidene]dioxy}pentadecanoic acid

(9S)-6-O-tert-butyldimethylsilyl-3,5-O-[(R)-4-methoxybenzylidene]-9,11-O-[(R)-2,4,6-trimethylbenzylidene]-9-dihydroerythronolide B

(9S)-3,5-O-[(R)-4-methoxybenzylidene]-9,11-O-[(R)-2,4,6-trimethylbenzylidene]-9-dihydroerythronolide B

(9S)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]-9-dihydroerythronolide B