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

Base Information

• Chemical Name: 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptitol
• CAS No.: 652993-98-1
• Molecular Formula: C₃₀H₃₅NO₆
• Molecular Weight: 505.611
• Mol file: 652993-98-1.mol

Synonyms:

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

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-heptitol

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

(E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene (537031-63-3) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptitol (652993-98-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 98 percent / OsO₄; NaIO₄ / tetrahydrofuran; H₂O; 2-methyl-propan-2-ol / 20 h / 20 °C

2: 79 percent / silica gel / ethyl acetate

3: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / 20 h / 20 °C

With sodium tetrahydroborate; sodium periodate; osmium(VIII) oxide; silica gel; In tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; tert-butyl alcohol;

DOI:10.1081/CAR-120026465

Reference yield:

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-aldehydo-D-glycero-D-ido-heptose (652993-93-6) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptitol (652993-98-1)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / silica gel / ethyl acetate

2: 89 percent / NaBH₄ / methanol; CH₂Cl₂ / 20 h / 20 °C

With sodium tetrahydroborate; silica gel; In methanol; dichloromethane; ethyl acetate;

DOI:10.1081/CAR-120026465

Reference yield: 21.0%

3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-3-deoxy-D-glycero-D-gulo-heptitol (652993-98-1) → 3-acetamido-2,6-anhydro-4,5,7-tri-O-benzyl-1-bromo-1,3-dideoxy-D-glycero-D-gulo-heptitol

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1081/CAR-120026465

upstream raw materials:

(E)-1-(2'-N-acetylamino-3',4',6'-tri-O-benzyl-2'-deoxy-α-D-glucopyranosyl)-2-propene

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