Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

Base Information

• Chemical Name: Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester
• CAS No.: 95058-17-6
• Molecular Formula: C₃₂H₃₄N₂O₉
• Molecular Weight: 590.63
• Mol file: 95058-17-6.mol

Synonyms:

Chemical Property of Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

There total 1 articles about Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl 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: 84.0%

benzoyl chloride (98-88-4) + D,L-(1r,2c,3c,4t,5t,6t)-1,4-bis(benzyloxycarbonylamino)-2,3-O-isopropyylidene-2,3,5,6-cyclohexanetetraol (95058-16-5) → Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (95058-17-6)

Guidance literature:

With pyridine; for 21h; Ambient temperature;

DOI:10.1246/cl.1984.1665

Reference yield: 70.0%

methanesulfonyl chloride (124-63-0) + Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (95058-17-6) → Benzoic acid (3aR,4S,5R,6S,7S,7aS)-4,7-bis-benzyloxycarbonylamino-6-methanesulfonyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (95058-18-7)

Guidance literature:

With pyridine;

DOI:10.1246/cl.1984.1665

Reference yield:

Benzoic acid (3aR,4S,5R,6S,7R,7aS)-4,7-bis-benzyloxycarbonylamino-6-hydroxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester (95058-17-6) → D,L-(1r,2c,4c,5t,6t)-2,5-bis(benzyloxycarbonylamino)-5-N-methyl-4,6-bis-O-tetrahydropyranyl-1,4,6-cyclohexanetriol (95058-13-2)

Guidance literature:

Multi-step reaction with 14 steps

1: 70 percent / pyridine

2: 93 percent / AcOH, H₂O / 2 h / 80 °C

3: 98 percent / NaI / dimethylformamide / 8 h / 100 °C

4: 96 percent / tri-n-butyl tin hydride, AIBN / tetrahydrofuran / Heating

5: 95 percent / pyridine / 3 h / 0 °C

6: 60 percent / dimethylformamide / 2.5 h / 60 - 65 °C

7: 64 percent / conc. NH₄OH / methanol

8: Ba(OH)2 / H₂O; dioxane

9: 74 percent / TsOH / dimethylformamide

10: hydrogen / 10percent Pd/C

11: Et₃N / H₂O; methanol / 3.5 h / Ambient temperature

12: 47 percent / Ba(OH)2*8H₂O / dioxane; H₂O / 7 h / 55 - 60 °C

13: LiAlH₄ / tetrahydrofuran / 1.5 h / Heating

With pyridine; barium dihydroxide; ammonium hydroxide; lithium aluminium tetrahydride; 2,2'-azobis(isobutyronitrile); water; hydrogen; tri-n-butyl-tin hydride; toluene-4-sulfonic acid; acetic acid; triethylamine; sodium iodide; palladium on activated charcoal; In tetrahydrofuran; 1,4-dioxane; methanol; water; N,N-dimethyl-formamide;

DOI:10.1246/cl.1984.1665

upstream raw materials:

benzoyl chloride

D,L-(1r,2c,3c,4t,5t,6t)-1,4-bis(benzyloxycarbonylamino)-2,3-O-isopropyylidene-2,3,5,6-cyclohexanetetraol

Downstream raw materials:

Benzoic acid (3aR,4S,5R,6S,7S,7aS)-4,7-bis-benzyloxycarbonylamino-6-methanesulfonyloxy-2,2-dimethyl-hexahydro-benzo[1,3]dioxol-5-yl ester

(1S,2S,3S,4R,6S)-6-Amino-3-methylamino-2,4-bis-(tetrahydro-pyran-2-yloxy)-cyclohexanol

D,L-(1r,2c,4c,5t,6t)-2-amino-5-formamido-4,6-bis-O-tetrahydropyranyl-1,4,6-cyclohexanetriol

D,L-(1r,2c,4c,5t,6t)-2-amino-5-benzyloxycarbonylamino-1-O,2-N-carbonyl-1,4,6-cyclohexanetriol