(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

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}pentadecanoic acid
• CAS No.: 944740-82-3
• Molecular Formula: C₅₃H₈₀O₁₀Si
• Molecular Weight: 905.298

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}pentadecanoic acid

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}pentadecanoic acid

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}pentadecanoic acid

There total 15 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}pentadecanoic acid 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: 100.0%

(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) → (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 (944740-82-3)

Guidance literature:

With disodium hydrogenphosphate; 3-chloro-benzenecarboperoxoic acid; In tetrahydrofuran; water; at 20 ℃; for 15h;

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}pentadecanoic acid (944740-82-3)

Guidance literature:

Multi-step reaction with 7 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

7.1: 100 percent / Na₂HPO₄; m-CPBA / tetrahydrofuran; H₂O / 15 h / 20 °C

With pyridine; disodium hydrogenphosphate; oil scarlet; 3 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; Dess-Martin periodane; ozone; acetic acid; (+)-10-camphorsulfonic acid; 3-chloro-benzenecarboperoxoic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; water; 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}pentadecanoic acid (944740-82-3)

Guidance literature:

Multi-step reaction with 8 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

8.1: 100 percent / Na₂HPO₄; m-CPBA / tetrahydrofuran; H₂O / 15 h / 20 °C

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

DOI:10.1016/j.tet.2007.02.044

upstream 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}pentadecanal

(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)-6-[(tert-butyldimethylsilyl)-oxy]-13-hydroxy-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

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