3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid

Base Information

• Chemical Name: 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid
• CAS No.: 182618-25-3
• Molecular Formula: C₃₀H₃₃NO₇
• Molecular Weight: 519.595
• Mol file: 182618-25-3.mol

Synonyms:3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid

Chemical Property of 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid

There total 15 articles about 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic 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:

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-gulo-heptose (652993-94-7) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid (182618-25-3)

Guidance literature:

With sodium chlorite; 2-methyl-but-2-ene; camphor-10-sulfonic acid; In tetrahydrofuran; isopropyl alcohol; at 20 ℃;

DOI:10.1016/S0040-4039(03)00818-9

Reference yield:

3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene (180778-41-0) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid (182618-25-3)

Guidance literature:

Multi-step reaction with 4 steps

1: NaH / dimethylformamide / 20 °C

2: 60 percent / (Ph₂Me)2IrCOD*PF₆ / tetrahydrofuran / 2 h / 20 °C

3: OsO₄; NaIO₄ / tetrahydrofuran; H₂O / 20 °C

4: NaClO₂; NaHPO₄; 2-methyl-2-butene / tetrahydrofuran; propan-2-ol / 20 °C

With sodium chlorite; sodium periodate; osmium(VIII) oxide; 2-methyl-but-2-ene; (Ph₂Me)2IrCOD*PF₆; camphor-10-sulfonic acid; sodium hydride; In tetrahydrofuran; water; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/S0040-4039(03)00818-9

Reference yield:

3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene (180778-36-3) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptonic acid (182618-25-3)

Guidance literature:

Multi-step reaction with 6 steps

1: NaOMe; MeOH

2: NaH / dimethylformamide / 20 °C

3: 87 percent / (Ph₂Me)2IrCOD*PF₆ / tetrahydrofuran / 2 h / 20 °C

4: O₃; Ph₃P / CH₂Cl₂

5: K₂CO₃ / CH₂Cl₂; methanol

6: NaClO₂; NaHPO₄; 2-methyl-2-butene / tetrahydrofuran; propan-2-ol / 20 °C

With methanol; sodium chlorite; 2-methyl-but-2-ene; (Ph₂Me)2IrCOD*PF₆; camphor-10-sulfonic acid; sodium methylate; sodium hydride; potassium carbonate; ozone; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; isopropyl alcohol;

DOI:10.1016/S0040-4039(03)00818-9

upstream raw materials:

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-gulo-heptose

3-(2'-N-acetylamino-2'-deoxy-β-D-glucopyranosyl)-1-propene

5-acetamido-6,7,9-tri-O-acetyl-4,8-anhydro-1,2,3,5-tetradeoxy-D-glycero-D-ido-non-enitol

3-(2'-acetamido-3',4',6-tri-O-acetyl-2'-deoxy-α-D-glucopyranosyl)-1-propene

Downstream raw materials:

(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid tert-butyl ester

(S)-3-[((2R,3R,4R,5S,6R)-3-Acetylamino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-carbonyl)-amino]-2-(9H-fluoren-9-ylmethoxycarbonylamino)-propionic acid