methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

Base Information

Chemical Name:methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate
CAS No.:368446-09-7
Molecular Formula:C₄₅H₅₆O₁₄SSi
Molecular Weight:881.083
Hs Code.:

methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

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Chemical Property of methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

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Technology Process of methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

There total 26 articles about methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate 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:

: 1053638-99-5
(2S,3S,4R,5R,6S)-3,5-Diacetoxy-4-benzoyloxy-6-{(S)-[(1R,2S,3R,5S,6S,7R)-6-benzyloxy-7-(tert-butyl-dimethyl-silanyloxy)-4-oxo-2-phenylsulfanyl-8-oxa-bicyclo[3.2.1]oct-3-yl]-hydroxy-methyl}-tetrahydro-pyran-2-carboxylic acid methyl ester

: 368446-09-7
methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

Guidance literature:: With sodium tetrahydroborate; In methanol; at 0 ℃; Yield given;
DOI:10.1016/S0040-4039(99)00432-3

Reference yield:

: 115140-20-0,129829-54-5,139342-54-4
(+/-)-(1R,4R,5R,6S)-6-endo-(benzyloxy)-5-exo-hydroxy-7-oxabicyclo<2.2.1>heptan-2-one

: 368446-09-7
methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

Guidance literature:: Multi-step reaction with 17 steps

1.1: 96 percent / 1H-imidazole / dimethylformamide

2.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C

2.2: 42 percent / tetrahydrofuran / 3 h / -60 - -20 °C

3.1: 8.24 g / 220 °C / 0.2 Torr

4.1: LDA / tetrahydrofuran / -78 °C

4.2: -78 - 20 °C

5.1: Et₂Zn / hexane; 1,2-dichloro-ethane / -20 - 20 °C

6.1: FeCl₃; pyridine / dimethylformamide / 60 °C

7.1: DBU; t-BuOOH / 2,2,4-trimethyl-pentane; CH₂Cl₂

8.1: NaBH₄ / methanol / 0 °C

9.1: pyridine

10.1: Bu₄NF / tetrahydrofuran

11.1: 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂

12.1: CF₃COOH / CH₂Cl₂ / 20 °C

13.1: DMAP / pyridine

14.1: 84 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

15.1: 68 percent / triflic acid / CH₂Cl₂

16.1: Hg(ClO₄)2*xH₂O / acetonitrile

16.2: Ag₂CO₃ / CHCl₃

17.1: CH₂Cl₂; tetrahydrofuran

17.2: tetrahydrofuran

17.3: CeCl₃*6H₂O; NaBH₄ / methanol

With pyridine; 1H-imidazole; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 2.1: Johnson and Zeller method / 4.1: Saegusa method / 5.1: Simmons-Smith cyclopropanation / 11.1: Dess-Martin oxidation / 14.1: Baeyer-Villiger oxidation / 17.1: Nozaki-Oshima condensation / 17.3: Luche's method;
DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M

Reference yield:

: 139391-31-4,139491-27-3
(1RS,4RS,5RS,6SR)-6-endo-(benzyloxy)-5-exo-{[(t-butyl)dimethylsilyl]oxy}-7-oxabicyclo[2.2.1]heptan-2-one

: 368446-09-7
methyl (7S)-3,5-di-O-acetyl-2,6-anhydro-4-O-benzoyl-7-C-{(1R,2S,3R,4S,5R,6S,7R)-6-endo-(benzyloxy)-7-exo-{[(tert-butyl)dimethylsilyl]oxy}-4-endo-hydroxy-2-exo-(phenylthio)-8-oxabicyclo[3.2.1]oct-3-endo-yl}-L-glycero-D-manno-heptonate

Guidance literature:: Multi-step reaction with 16 steps

1.1: BuLi / hexane; tetrahydrofuran / 0.5 h / -25 °C

1.2: 42 percent / tetrahydrofuran / 3 h / -60 - -20 °C

2.1: 8.24 g / 220 °C / 0.2 Torr

3.1: LDA / tetrahydrofuran / -78 °C

3.2: -78 - 20 °C

4.1: Et₂Zn / hexane; 1,2-dichloro-ethane / -20 - 20 °C

5.1: FeCl₃; pyridine / dimethylformamide / 60 °C

6.1: DBU; t-BuOOH / 2,2,4-trimethyl-pentane; CH₂Cl₂

7.1: NaBH₄ / methanol / 0 °C

8.1: pyridine

9.1: Bu₄NF / tetrahydrofuran

10.1: 1,1,1-tris(acetyloxy)-1,1-dihydro-1,2-benziodoxol-3(1H)-one / CH₂Cl₂

11.1: CF₃COOH / CH₂Cl₂ / 20 °C

12.1: DMAP / pyridine

13.1: 84 percent / mCPBA; NaHCO₃ / CH₂Cl₂ / 20 °C

14.1: 68 percent / triflic acid / CH₂Cl₂

15.1: Hg(ClO₄)2*xH₂O / acetonitrile

15.2: Ag₂CO₃ / CHCl₃

16.1: CH₂Cl₂; tetrahydrofuran

16.2: tetrahydrofuran

16.3: CeCl₃*6H₂O; NaBH₄ / methanol

With pyridine; tert.-butylhydroperoxide; dmap; sodium tetrahydroborate; n-butyllithium; mercury(II) perchlorate; trifluorormethanesulfonic acid; tetrabutyl ammonium fluoride; diethylzinc; iron(III) chloride; sodium hydrogencarbonate; Dess-Martin periodane; 1,8-diazabicyclo[5.4.0]undec-7-ene; 3-chloro-benzenecarboperoxoic acid; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; pyridine; methanol; 2,2,4-trimethylpentane; hexane; dichloromethane; 1,2-dichloro-ethane; N,N-dimethyl-formamide; acetonitrile; 1.1: Johnson and Zeller method / 3.1: Saegusa method / 4.1: Simmons-Smith cyclopropanation / 10.1: Dess-Martin oxidation / 13.1: Baeyer-Villiger oxidation / 16.1: Nozaki-Oshima condensation / 16.3: Luche's method;
DOI:10.1002/1522-2675(20010613)84:6<1363::AID-HLCA1363>3.0.CO;2-M