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Technology Process of (2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

Base Information
  • Chemical Name:(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
  • CAS No.:115031-02-2
  • Molecular Formula:C49H56O10
  • Molecular Weight:804.978
  • Hs Code.:
(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

Synonyms:

Suppliers and Price of (2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
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Chemical Property of (2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
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Technology Process of (2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

There total 12 articles about (2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid 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:

benzaldehyde
100-52-7

benzaldehyde

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
115031-02-2,115075-74-6

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

Guidance literature:
Multi-step reaction with 6 steps
1: pyridinium tosylate / benzene / 2 h / 80 °C
2: !) nBuLi; 2) PhSeCl; 3) 3-chloroperoxybenzoic acid, aq. NaHCO3 / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min; 3) THF, 10 deg C, 20 min
3: 1) tBuLi; 3) Na-Hg, Na2HPO4 / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C to room temp.; 3) MeOH, THF, -30 deg C, 30 min
4: TBAF / tetrahydrofuran / 2 h / 65 °C
5: 1) (COCl)2, DMSO, 2) Et3N / 1) -60 deg C, 20 min, 2) -60 deg C to room temp., 1h
6: NaO2Cl, KH2PO4, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H2O / 0.5 h / Ambient temperature
With sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)96835-7

Reference yield:

(+)-(1S,3S,4S,6S)-6-<(tert-butyldiphenylsilyloxy)methyl>-4-methyl-1-<1-methylene-3-(phenylsulphonyl)propyl>-1,3-cyclohexanediol
115075-76-8

(+)-(1S,3S,4S,6S)-6-<(tert-butyldiphenylsilyloxy)methyl>-4-methyl-1-<1-methylene-3-(phenylsulphonyl)propyl>-1,3-cyclohexanediol

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
115031-02-2,115075-74-6

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

Guidance literature:
Multi-step reaction with 7 steps
1: 1) BH3*Me2S; 2) NaOH, aq. H2O2 / 1) THF, -20 deg C, 16 h; 2) H2O, room temp., 30 min
2: pyridinium tosylate / benzene / 2 h / 80 °C
3: !) nBuLi; 2) PhSeCl; 3) 3-chloroperoxybenzoic acid, aq. NaHCO3 / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min; 3) THF, 10 deg C, 20 min
4: 1) tBuLi; 3) Na-Hg, Na2HPO4 / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C to room temp.; 3) MeOH, THF, -30 deg C, 30 min
5: TBAF / tetrahydrofuran / 2 h / 65 °C
6: 1) (COCl)2, DMSO, 2) Et3N / 1) -60 deg C, 20 min, 2) -60 deg C to room temp., 1h
7: NaO2Cl, KH2PO4, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H2O / 0.5 h / Ambient temperature
With sodium hydroxide; sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; dimethylsulfide borane complex; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)96835-7

Reference yield:

(1R,3S,4S,6S)-1-((S)-3-Benzenesulfonyl-1-hydroxymethyl-propyl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-cyclohexane-1,3-diol
115030-95-0,115075-71-3,127854-64-2,127854-65-3

(1R,3S,4S,6S)-1-((S)-3-Benzenesulfonyl-1-hydroxymethyl-propyl)-6-(tert-butyl-diphenyl-silanyloxymethyl)-4-methyl-cyclohexane-1,3-diol

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid
115031-02-2,115075-74-6

(2S,6R,7S,9R,10R)-10-Benzoyloxy-5-[(2E,6E)-8-(4-benzoyloxy-1,7-dioxa-spiro[5.5]undec-2-yl)-6-methyl-octa-2,6-dien-(E)-ylidene]-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecane-7-carboxylic acid

Guidance literature:
Multi-step reaction with 6 steps
1: pyridinium tosylate / benzene / 2 h / 80 °C
2: !) nBuLi; 2) PhSeCl; 3) 3-chloroperoxybenzoic acid, aq. NaHCO3 / 1) THF, -78 deg C, 30 min; 2) THF, -78 deg C, 15 min; 3) THF, 10 deg C, 20 min
3: 1) tBuLi; 3) Na-Hg, Na2HPO4 / 1) THF, -78 deg C, 20 min; 2) THF, -78 deg C to room temp.; 3) MeOH, THF, -30 deg C, 30 min
4: TBAF / tetrahydrofuran / 2 h / 65 °C
5: 1) (COCl)2, DMSO, 2) Et3N / 1) -60 deg C, 20 min, 2) -60 deg C to room temp., 1h
6: NaO2Cl, KH2PO4, 2-methylbut-2-ene / 2-methyl-propan-2-ol; H2O / 0.5 h / Ambient temperature
With sodium chlorite; disodium hydrogenphosphate; potassium dihydrogenphosphate; sodium amalgam; 2-methyl-but-2-ene; oxalyl dichloride; tetrabutyl ammonium fluoride; tert.-butyl lithium; pyridinium p-toluenesulfonate; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; water; tert-butyl alcohol; benzene;
DOI:10.1016/S0040-4039(00)96835-7
upstream raw materials:

C49H56O9

1,4-Pentadiene

Benzoic acid 2-((E)-3-methyl-6-oxo-hex-2-enyl)-1,7-dioxa-spiro[5.5]undec-4-yl ester

(2R,5S,6S,8S,9S,11S)-5-((E)-2-Benzenesulfonyl-vinyl)-11-(tert-butyl-diphenyl-silanyloxymethyl)-9-methyl-2-phenyl-1,3-dioxa-spiro[5.5]undecan-8-ol

Downstream raw materials:

C35H46O7

C35H46O7

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