(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Base Information

Chemical Name:(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester
CAS No.:1053718-78-7
Molecular Formula:C₄₀H₅₈O₁₂Si
Molecular Weight:758.979
Hs Code.:

(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Synonyms:

Suppliers and Price of (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Supply Marketing:

Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

Manufacturers and distributors:

Manufacture/Brand
Chemicals and raw materials
Packaging
price

Total 0 raw suppliers

Chemical Property of (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Chemical Property:

Purity/Quality:

Safty Information:

Pictogram(s):
Hazard Codes:

MSDS Files:

Useful:

Technology Process of (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

There total 18 articles about (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester 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:

: (1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-formyl-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,5-dicarboxylic acid di-tert-butyl ester

: 1053718-78-7
(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; In water; tert-butyl alcohol; for 8h; Ambient temperature;
DOI:10.1021/jo961534e

Reference yield:

: 138709-45-2
1,6-Anhydro-2,3-di-O-benzyl-β-D-gluco-hexopyrano-4-ulose

: 1053718-78-7
(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Guidance literature:: Multi-step reaction with 18 steps

1: 2.) NaHCO₃, aq. H₂O₂ / 1.) THF, -78 deg C, 30 min; -78 deg C to -15 deg C 2 h, 2.) THF, MeOH, reflux, 12 h

2: 100 percent / imidazole / dimethylformamide / Ambient temperature

3: Ac₂O / 1.5 h / 68 °C

4: MeONa / methanol / 2 h / Ambient temperature

5: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

6: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

7: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

8: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

9: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

10: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

11: TBAF / tetrahydrofuran / 1 h / 0 °C

12: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

13: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h

14: CH₂Cl₂ / Ambient temperature

15: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) room temperature, 30 min

16: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 30 min, 2.) room temperature, 1 h

17: imidazole / dimethylformamide / 0.5 h / Ambient temperature

18: NaClO2, NaH2PO4, β-isoamylene / 2-methyl-propan-2-ol; H2O / 8 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; dipyridinium dichromate; cerium(III) chloride; 2-methyl-but-2-ene; dimethylsulfide; Celite; tetrabutyl ammonium fluoride; dihydrogen peroxide; tert.-butyl lithium; sodium methylate; acetic anhydride; sodium hydrogencarbonate; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo961534e

Reference yield:

: 168103-69-3
1,6-Anhydro-2,3-di-O-benzyl-4-(hydroxymethyl)-β-D-galactopyranose

: 1053718-78-7
(1S,3S,4S,5R,6R,7R)-6,7-Bis-benzyloxy-1-[3-(tert-butyl-dimethyl-silanyloxy)-propyl]-4-hydroxy-2,8-dioxa-bicyclo[3.2.1]octane-3,4,5-tricarboxylic acid 3,5-di-tert-butyl ester

Guidance literature:: Multi-step reaction with 17 steps

1: 100 percent / imidazole / dimethylformamide / Ambient temperature

2: Ac₂O / 1.5 h / 68 °C

3: MeONa / methanol / 2 h / Ambient temperature

4: 1.) p-TsOH, 2.) Celite, 4A NS, PDC / 2.) CH₂Cl₂, room temperature, 3 h

5: 1.) CeCl₃, 3.) 2N HCl / 1.) THF, Et₂O, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 6 h, 3.) THF, reflux, 3 h

6: 1.) DMSO, TFAA, 2.) Et₃N / 1.) CH₂Cl₂, -78 deg C, 45 min, 2.) -78 deg C to room temperature, 30 min

7: 1.) t-BuLi / 1.) THF, -78 deg C, 10 min, 2.) THF, -78 deg C, 1 h

8: 98 percent / imidazole / dimethylformamide / 0.75 h / Ambient temperature

9: 1.) CeCl₃ / 1.) THF, -78 deg C, 30 min, 2.) THF, -78 deg C to -50 deg C, 3 h

10: TBAF / tetrahydrofuran / 1 h / 0 °C

11: Dess-Martin periodinane / CH₂Cl₂ / Ambient temperature

12: NaClO₂, NaH₂PO₄, 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.5 h

13: CH₂Cl₂ / Ambient temperature

14: 1.) O₃, 2.) NaBH₄ / 1.) CH₂Cl₂, MeOH, -78 deg C, 2.) room temperature, 30 min

15: 1.) O₃, 2.) Me₂S / 1.) CH₂Cl₂, MeOH, -78 deg C, 30 min, 2.) room temperature, 1 h

16: imidazole / dimethylformamide / 0.5 h / Ambient temperature

17: NaClO2, NaH2PO4, β-isoamylene / 2-methyl-propan-2-ol; H2O / 8 h / Ambient temperature

With 1H-imidazole; hydrogenchloride; sodium chlorite; sodium tetrahydroborate; sodium dihydrogenphosphate; dipyridinium dichromate; cerium(III) chloride; 2-methyl-but-2-ene; dimethylsulfide; Celite; tetrabutyl ammonium fluoride; tert.-butyl lithium; sodium methylate; acetic anhydride; Dess-Martin periodane; toluene-4-sulfonic acid; ozone; dimethyl sulfoxide; triethylamine; trifluoroacetic anhydride; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1021/jo961534e