3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic acid

Base Information

• Chemical Name: 3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic acid
• CAS No.: 55728-21-7
• Molecular Formula: C13H14N2O10
• Molecular Weight: 358.26
• Mol file: 55728-21-7.mol

Synonyms:3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic acid;Octosyl acid A

Chemical Property of 3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic acid

Chemical Property:

• Melting Point: 260 - 263 °C
• PSA: 188.38000
• LogP: -2.90390

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic acid

There total 42 articles about 3,7-Anhydro-1-[5-carboxy-3,4-dihydro-2,4-dioxopyrimidin-1(2H)-yl]-1,6-dideoxy-D-glycero-β-D-allo-octofuranuronic 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: 78.0%

methyl 3,7-anhydro-1,6-dideoxy-1-<3,4-dihydro-5-(methoxycarbonyl)-2,4-dioxo-1(2H)-pyrimidinyl>-L-glycero-β-D-allo-octofuranuronate (116185-24-1) → octosyl acid A (55728-21-7)

Guidance literature:

With lithium hydroxide; Dowex IR-40 ; water; In tetrahydrofuran; for 2h; Ambient temperature;

DOI:10.1021/ja00230a024

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → octosyl acid A (55728-21-7)

Guidance literature:

Multi-step reaction with 17 steps

1: 1.) zinc chloride, 2.) trifluoroacetic acid / 1.) THF, r.t., 9 h, 2.) r.t., 3 h

2: 11.5 g / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -78 °C

3: 13.5 g / 50 percent NaH / dimethylformamide; paraffin / 0 °C

4: 1.) NaIO₄, OsO₄, 2.) 5 percent aq. K₂CO₃ / 1.) dioxane/H₂O, r.t., overnight, 2.) MeOH, r.t., 1 h

5: 86 percent / Ag₂CO₃-Celite / xylene / 1.5 h / Heating

6: lithium hydroxide monohydrate, H₂O / 1,2-dimethoxy-ethane / 2 h / 50 °C

7: 1.) 50 percent NaH, 2.) 1 N HCl / dimethylformamide; paraffin

8: diethyl ether; methanol

9: 62 percent / DDQ, H₂O / CH₂Cl₂ / 24 h

10: 83 percent / triethylamine / CH₂Cl₂ / 1.) -20 deg C, 3 h, 2.) 0 deg C, 3 h

11: 1 N HCl / methanol / 1.5 h / Heating

12: 248 mg / pyridine / 5 h

13: 1.) acetic acid, conc. H₂SO₄, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₃CN, 0 deg C, 3 h; r.t., 5 h

14: 84 percent / NaOMe, MeOH / 1.5 h

15: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1 h, 2.) DMF, 60 deg C, 8 h; r.t., 9 h

16: 80 percent / H₂ / Pd(OH)2 / tetrahydrofuran / 0.25 h

17: 78 percent / 1.) H₂O, LiOH*H₂O, 2.) Dowex IR-40 (1+) form> / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; Dowex IR-40 ; sulfuric acid; water; hydrogen; sodium methylate; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; triethylamine; cesium fluoride; silver carbonate; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; zinc(II) chloride; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; paraffin; xylene;

DOI:10.1021/ja00230a024

Reference yield:

methyl 5,9-anhydro-6,8-dideoxy-2,3-O-(1-methylethylidene)-β-D-allo-non-8-enofuranosid-7-ulose (99441-05-1) → octosyl acid A (55728-21-7)

Guidance literature:

Multi-step reaction with 16 steps

1: 11.5 g / CeCl₃*7H₂O, NaBH₄ / methanol / 1 h / -78 °C

2: 13.5 g / 50 percent NaH / dimethylformamide; paraffin / 0 °C

3: 1.) NaIO₄, OsO₄, 2.) 5 percent aq. K₂CO₃ / 1.) dioxane/H₂O, r.t., overnight, 2.) MeOH, r.t., 1 h

4: 86 percent / Ag₂CO₃-Celite / xylene / 1.5 h / Heating

5: lithium hydroxide monohydrate, H₂O / 1,2-dimethoxy-ethane / 2 h / 50 °C

6: 1.) 50 percent NaH, 2.) 1 N HCl / dimethylformamide; paraffin

7: diethyl ether; methanol

8: 62 percent / DDQ, H₂O / CH₂Cl₂ / 24 h

9: 83 percent / triethylamine / CH₂Cl₂ / 1.) -20 deg C, 3 h, 2.) 0 deg C, 3 h

10: 1 N HCl / methanol / 1.5 h / Heating

11: 248 mg / pyridine / 5 h

12: 1.) acetic acid, conc. H₂SO₄, 2.) trimethylsilyl triflate / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₃CN, 0 deg C, 3 h; r.t., 5 h

13: 84 percent / NaOMe, MeOH / 1.5 h

14: 1.) n-Bu₂SnO, 2.) CsF / 1.) MeOH, reflux, 1 h, 2.) DMF, 60 deg C, 8 h; r.t., 9 h

15: 80 percent / H₂ / Pd(OH)2 / tetrahydrofuran / 0.25 h

16: 78 percent / 1.) H₂O, LiOH*H₂O, 2.) Dowex IR-40 (1+) form> / tetrahydrofuran / 2 h / Ambient temperature

With pyridine; hydrogenchloride; methanol; lithium hydroxide; sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; cerium(III) chloride; trimethylsilyl trifluoromethanesulfonate; Dowex IR-40 ; sulfuric acid; water; hydrogen; sodium methylate; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; acetic acid; triethylamine; cesium fluoride; silver carbonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; palladium dihydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide; paraffin; xylene;

DOI:10.1021/ja00230a024

upstream raw materials:

methyl 1-uracil-5-carboxylate

methyl 2,4-dihydroxypyrimidine-5-carboxylate

methyl 1-<8-O-allyl-3,7-anhydro-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate

methyl 1-<3,7-anhydro-2-O-benzoyl-5-O-benzyl-6-deoxy-β-L-glycero-D-allo-octofuranos-(1,4)-yl>uracil-5-carboxylate