(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

Base Information

Chemical Name:(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one
CAS No.:192574-00-8
Molecular Formula:C₄₉H₆₆O₈Si
Molecular Weight:811.144
Hs Code.:

(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

Synonyms:(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

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Chemical Property of (2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

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Technology Process of (2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

There total 9 articles about (2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one 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: 54.0%

: (Z)-(5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-5-hydroxy-12-methyl-4-methylene-13-phenyl-tridec-2-en-7-one

: 192574-00-8
(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

Guidance literature:: With potassium osmate(VI); methanesulfonamide; 1,4-bis(9-O-dihydroquinidine)phthalazine; In tert-butyl alcohol; at 20 ℃; for 16h;
DOI:10.1016/S0040-4039(97)00885-X

Reference yield:

: 5445-77-2,63262-79-3,78964-59-7,42307-59-5
(2R)-2-methyl-3-phenylpropanal

: 192574-00-8
(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

Guidance literature:: Multi-step reaction with 7 steps

1: 1.) B-methoxybis(2-isocaranyl)borane, 2.) H₂O₂ / 1.) Et₂O, -78 deg C, 4 h, 2.) aq. NaOH, reflux, 16 h

2: 2.) Oxone / 1.) AIBN / 1.) PhMe, 90 deg C, 72 h, 2.) MeOH/H₂O, 20 deg C, 4 h

3: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

4: 1.) n-BuLi, 2.) (COCl)2/DMSO, 3.) Et₃N / 1.) THF/Et₂O (5:1), -78 deg C, 1h; -40 deg C, 70 min, 2.) CH₂Cl₂, -78 deg C, 65 min, 3.) to 0 deg C, 40 min

5: 6percent Na(Hg), Na₂HPO₄ / methanol; tetrahydrofuran / 2 h / 20 °C

6: HF/py / pyridine; tetrahydrofuran / 4.5 h / 20 °C

7: 54 percent / (DHQD)2PHAL/K₂OsO₄*2H₂O, MeSO₂NH₂ / 2-methyl-propan-2-ol / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; Oxone; potassium osmate(VI); disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; methanesulfonamide; B-methoxy-bis(2-isocaranyl)borane; hydrogen fluoride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; pyridine; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)00885-X

Reference yield:

: 100-39-0
benzyl bromide

: 192574-00-8
(2R,3S,5S,6S,11R,12R)-1,6-Bis-benzyloxy-3-benzyloxymethyl-11-(tert-butyl-dimethyl-silanyloxy)-2,3,5-trihydroxy-12-methyl-4-methylene-13-phenyl-tridecan-7-one

Guidance literature:: Multi-step reaction with 9 steps

1: 88 percent / LDA, LiCl / tetrahydrofuran / 0.33 h / 0 °C

2: 1.) LiAl(OEt)3H, 2.) HCl / 1.) hexane/THF, -78 deg C to 0 deg C, 1 h, 2.) TFA, 20 deg C, 5 min

3: 1.) B-methoxybis(2-isocaranyl)borane, 2.) H₂O₂ / 1.) Et₂O, -78 deg C, 4 h, 2.) aq. NaOH, reflux, 16 h

4: 2.) Oxone / 1.) AIBN / 1.) PhMe, 90 deg C, 72 h, 2.) MeOH/H₂O, 20 deg C, 4 h

5: 96 percent / 2,6-lutidine / CH₂Cl₂ / 0.33 h / -78 °C

6: 1.) n-BuLi, 2.) (COCl)2/DMSO, 3.) Et₃N / 1.) THF/Et₂O (5:1), -78 deg C, 1h; -40 deg C, 70 min, 2.) CH₂Cl₂, -78 deg C, 65 min, 3.) to 0 deg C, 40 min

7: 6percent Na(Hg), Na₂HPO₄ / methanol; tetrahydrofuran / 2 h / 20 °C

8: HF/py / pyridine; tetrahydrofuran / 4.5 h / 20 °C

9: 54 percent / (DHQD)2PHAL/K₂OsO₄*2H₂O, MeSO₂NH₂ / 2-methyl-propan-2-ol / 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; hydrogenchloride; Oxone; potassium osmate(VI); disodium hydrogenphosphate; n-butyllithium; sodium amalgam; oxalyl dichloride; methanesulfonamide; B-methoxy-bis(2-isocaranyl)borane; hydrogen fluoride; dihydrogen peroxide; pyridine hydrogenfluoride; dimethyl sulfoxide; lithium triethoxyaluminum hydride; 1,4-bis(9-O-dihydroquinidine)phthalazine; triethylamine; lithium chloride; lithium diisopropyl amide; 2,2'-azobis(isobutyronitrile); In tetrahydrofuran; pyridine; methanol; dichloromethane; tert-butyl alcohol;
DOI:10.1016/S0040-4039(97)00885-X