(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Base Information

Chemical Name:(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol
CAS No.:608143-19-7
Molecular Formula:C₅₆H₉₃NO₁₁Si
Molecular Weight:984.44
Hs Code.:

(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Synonyms:(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

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Chemical Property of (3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

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Technology Process of (3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

There total 16 articles about (3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol 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: 86.0%

: 31197-41-8,76505-19-6
crotyltributylstannane

: 608143-18-6
(2R,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-4-[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanal

: 608143-19-7
(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Guidance literature:: crotyltributylstannane; (2R,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-4-[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanal; With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃; for 10h;

With sodium hydroxide; In dichloromethane; at 20 ℃; for 14h; Further stages.;
DOI:10.1016/j.tet.2007.02.044

Reference yield: 84.0%

: 35998-93-7
tri-n-butylcrotyltin

: 608143-18-6
(2R,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-4-[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecanal

: 608143-19-7
(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 ℃;
DOI:10.1002/anie.200351136

Reference yield:

: 123163-78-0
(2S,3R)-3-<(benzyloxy)methoxy>-2-methylpentanal

: 608143-19-7
(3S,4R,5R,6R,7R,9R,10S,11S,12S,13S,14R)-14-(benzyloxymethoxy)-6-O-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-3,5,7,9,11,13-hexamethyl-7-[(triethylsilyl)oxy]-10,12-{[(R)-2,4,6-trimethylbenzylidene]dioxy}hexadecen-4-ol

Guidance literature:: Multi-step reaction with 9 steps

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

1.2: 83 percent / tetrahydrofuran / 2 h / -78 - -20 °C

2.1: 93 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 12 h / -25 - -20 °C

3.1: 90 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

4.1: 92 percent / LiBH₄ / diethyl ether / 5 h / 20 °C

5.1: 42 percent / molecular sieves 4 Angstroem; silver triflate; 2,6-di-tert-butylpyridine / CH₂Cl₂; toluene / 4 h / 20 °C

6.1: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.25 h

7.1: 98 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h / 0 °C

8.1: 91 percent / oxalyl chloride; DMSO; N-methylmorpholine / CH₂Cl₂ / 0.5 h / -78 - 20 °C

9.1: BF₃*OEt₂ / CH₂Cl₂ / 10 h / -78 °C

9.2: 86 percent / aq. NaOH / CH₂Cl₂ / 14 h / 20 °C

With 4-methyl-morpholine; lithium borohydride; 2,6-di-tert-butyl-pyridine; oxalyl dichloride; 4 A molecular sieve; boron trifluoride diethyl etherate; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; dimethyl sulfoxide; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile; 8.1: Swern oxidation;
DOI:10.1016/j.tet.2007.02.044