(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Base Information

• Chemical Name: (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane
• CAS No.: 188786-09-6
• Molecular Formula: C₅₆H₉₂O₈Si₂
• Molecular Weight: 949.513
• Mol file: 188786-09-6.mol

Synonyms:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Chemical Property of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

There total 12 articles about (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane 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: 83.0%

(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) + mesitaldehyde dimethylacetal (64761-29-1) → (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane (188786-09-6)

Guidance literature:

With (+)-10-camphorsulfonic acid; In dichloromethane; at 20 ℃; for 3h;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonan-7-one (188785-99-1) → (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane (188786-09-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

1.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

2.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

3.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

With tetramethylammonium borohydride; acetic acid; (+)-10-camphorsulfonic acid; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2007.02.044

Reference yield:

(2S,3R,4R,6R)-1,4-bis[(tert-butyldimethylsilyl)oxy]-7,7-(ethylenedithio)-3-[(4-methoxybenzyl)oxy]-2,4,6-trimethylnonane (188785-95-7) → (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-[(benzyloxy)methoxy]-1,4-bis[(tert-butyldimethylsilyl)oxy]-3-[(4-methoxybenzyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane (188786-09-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 85 percent / CaCO₃; Hg(ClO₄)2 / tetrahydrofuran; H₂O / 0.25 h / 20 °C

2.1: lithium hexamethyldisilazide / tetrahydrofuran / 2 h / -78 - -15 °C

2.2: 86 percent / tetrahydrofuran / 1 h / -78 °C

3.1: 73 percent / acetic acid; Me₄NBH₄ / acetonitrile / 70 h / -10 - -6 °C

4.1: 83 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

With mercury(II) perchlorate; tetramethylammonium borohydride; acetic acid; (+)-10-camphorsulfonic acid; calcium carbonate; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; water; acetonitrile;

DOI:10.1016/j.tet.2007.02.044

upstream raw materials:

mesitaldehyde dimethylacetal

(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,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)-7,7-(ethylenedithio)-1,3-{[(R)-4-methoxybenzylidene]dioxy}-2,4,6-trimethylnonan-4-ol

Downstream raw materials:

(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

(9S)-9-dihydro-5-O-(2-O-(methoxycarbonyl)-β-D-desosaminyl)-9,11-O-[(R)-2,4,6-trimethylbenzylidene]erythronolide B

(3S,4R,5S,6R,7R,9R,10S,11S,12S,13S,14R)-14-[(benzyloxy)methoxy]-7-[(tert-butyldimethylsilyl)oxy]-6-[(4-methoxybenzyl)oxy]-3,5,7,9,11,13-hexamethyl-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadec-1-en-4-ol

(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