(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Base Information

Chemical Name:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane
CAS No.:944740-93-6
Molecular Formula:C₅₈H₁₀₁NO₁₁Si₂
Molecular Weight:1044.61
Hs Code.:

(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Synonyms:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

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Chemical Property of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

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Technology Process of (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

There total 11 articles about (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-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: 98.0%

: 79271-56-0
triethylsilyl trifluoromethyl sulfonate

: 944740-91-4
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane-1,4-diol

: 944740-93-6
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 ℃; for 2h;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

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

: 944740-93-6
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: Multi-step reaction with 7 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

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

Reference yield:

: 149820-11-1
(2S,3R,4R,6R,8R,9S,10R,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3,4-(carbonyldioxy)-9-hydroxy-2,4,6,8,10-pentamethyldecan-7-one

: 944740-93-6
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-1,4-bis[(triethylsilyl)oxy]-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane

Guidance literature:: Multi-step reaction with 6 steps

1: 93 percent / tetramethylammonium triacetoxyborohydride; acetic acid / acetonitrile / 12 h / -25 - -20 °C

2: 90 percent / (+)-10-camphorsulfonic acid / CH₂Cl₂ / 3 h / 20 °C

3: 92 percent / LiBH₄ / diethyl ether / 5 h / 20 °C

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

5: 99 percent / tetrabutylammonium fluoride / tetrahydrofuran / 1.25 h

6: 98 percent / ethyldiisopropylamine / CH₂Cl₂ / 2 h / 0 °C

With lithium borohydride; 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; tetrabutyl ammonium fluoride; silver trifluoromethanesulfonate; acetic acid; (+)-10-camphorsulfonic acid; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; diethyl ether; dichloromethane; toluene; acetonitrile;
DOI:10.1016/j.tet.2007.02.044