Arabinuronic acid, gamma-lactone (6CI,9CI)

Base Information

• Chemical Name: Arabinuronic acid, gamma-lactone (6CI,9CI)
• CAS No.: 98021-64-8
• Molecular Formula: C₅H₆O₅
• Molecular Weight: 146.1
• Mol file: 98021-64-8.mol

Synonyms:Arabinuronic acid, gamma-lactone (6CI,9CI)

Chemical Property of Arabinuronic acid, gamma-lactone (6CI,9CI)

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Arabinuronic acid, gamma-lactone (6CI,9CI)

There total 1 articles about Arabinuronic acid, gamma-lactone (6CI,9CI) 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:

D-glucurono-6,3-lactone (63-29-6,487-44-5,575-64-4,14362-29-9,18281-92-0,26623-21-2) → D-arabinurono-2,5-lactone (98021-64-8)

Guidance literature:

With methanol; sodium periodate; disodium hydrogenphosphate; at 0 - 20 ℃; for 13h;

DOI:10.1002/ejoc.200390133

Reference yield:

D-arabinurono-2,5-lactone (98021-64-8) → methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate (1389271-16-2) + C24H35NO11S3Si (1403601-11-5)

Guidance literature:

Multi-step reaction with 8 steps

1.1: pyridine / methanol; water / 15 h / 20 °C

2.1: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

3.1: manganese(IV) oxide / toluene / 79 h / 70 °C

4.1: camphor-10-sulfonic acid / 67 h / 50 °C

5.1: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

6.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 1.5 h / 80 °C

7.1: boron trifluoride diethyl etherate; tri-n-butyl-tin hydride / toluene / -78 - 20 °C / Inert atmosphere

7.2: 4 h / 20 °C / Inert atmosphere

8.1: pyridine; dmap / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; dmap; manganese(IV) oxide; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tri-n-butyl-tin hydride; 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; In methanol; water; ethyl acetate; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2012.06.022

Reference yield:

D-arabinurono-2,5-lactone (98021-64-8) → methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate (1389271-11-7) + C24H35NO11S3Si (1389271-02-6)

Guidance literature:

Multi-step reaction with 6 steps

1: pyridine / methanol; water / 15 h / 20 °C

2: 1H-imidazole / N,N-dimethyl-formamide / 3 h / 0 °C / Inert atmosphere

3: manganese(IV) oxide / toluene / 79 h / 70 °C

4: camphor-10-sulfonic acid / 67 h / 50 °C

5: 1H-imidazole / N,N-dimethyl-formamide / 18 h / 20 °C

6: pyridine / 0 - 20 °C / Inert atmosphere

With pyridine; 1H-imidazole; manganese(IV) oxide; camphor-10-sulfonic acid; In methanol; water; N,N-dimethyl-formamide; toluene;

DOI:10.1016/j.tet.2012.06.022

upstream raw materials:

D-glucurono-6,3-lactone

Downstream raw materials:

methyl 2-[(1R,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

C₂₄H₃₅NO₁₁S₃Si

methyl 2-[(1S,2R,3S)-3-(benzyloxycarbonyl)-1-methanesulfonyloxy-2-hydroxy-3-(tert-butyl-dimethylsilyloxy)-propyl]-thiazole-4-carboxylate

C₂₄H₃₅NO₁₁S₃Si

Refernces

• 1、 Tremmel, Peter,Brand, Joerg,Knapp, Volker,Geyer, Armin. "Side-chain-functionalized dipeptides derived from 6,5-fused bicyclic thiazolidinlactams". . p. 878 - 884. Retrieved 2007/10/03.