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

Base Information

Chemical Name:(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecan-4-ol
CAS No.:608143-16-4
Molecular Formula:C₅₂H₈₇NO₁₁Si
Molecular Weight:930.348
Hs Code.:

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

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

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

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

There total 12 articles about (2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecan-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: 42.0%

: C₁₄H₂₁N₃O₄S

: 608143-15-3
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane-3,4-diol

: C₅₂H₈₇NO₁₁Si

: 608143-16-4
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecan-4-ol

Guidance literature:: With 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at 20 ℃; for 4h;
DOI:10.1016/j.tet.2007.02.044

Reference yield:

: 138603-63-1
1-(2-pyrimidinethio) 3,4,6-trideoxy-2-O-methoxycarbonyl-3-(dimethylamino)-D-xylo-hexopyranoside

: 608143-15-3
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecane-3,4-diol

: C₅₂H₈₇NO₁₁Si

: 608143-16-4
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecan-4-ol

Guidance literature:: With 2,6-di-tert-butyl-pyridine; 4 A molecular sieve; silver trifluoromethanesulfonate; In dichloromethane; toluene; at 20 ℃;
DOI:10.1002/anie.200351136

Reference yield:

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

: 608143-16-4
(2S,3R,4R,6R,7S,8S,9S,10S,11R)-11-(benzyloxymethoxy)-1-[(tert-butyldimethylsilyl)oxy]-3-[(2'-O-methoxycarbonyl-α-D-desosaminyl)oxy]-2,4,6,8,10-pentamethyl-7,9-{[(R)-2,4,6-trimethylbenzylidene]dioxy}tridecan-4-ol

Guidance literature:: Multi-step reaction with 5 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

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