(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol

Base Information

• Chemical Name: (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol
• CAS No.: 727989-26-6
• Molecular Formula: C₂₀H₂₁NO₆
• Molecular Weight: 371.39
• Mol file: 727989-26-6.mol

Synonyms:(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol

Chemical Property of (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol

There total 1 articles about (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol 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: 81.0%

(diethoxymethyl)benzene (774-48-1) + (4R,5S,6R)-N-benzyloxycarbonyl-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6=tetrahydro-2H-1,2-oxazine (568586-65-2) → (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol (727989-26-6)

Guidance literature:

With camphor-10-sulfonic acid; In chloroform; for 1h; Heating;

DOI:10.1071/CH03227

Reference yield: 82.0%

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol (727989-26-6) + 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate (92052-29-4) → (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-5-(tetra-O-acetyl-β-D-glucopyranosyl)oxy-3-aza-2,7,9-trioxabicyclo[4.4.0]decane (727989-27-7)

Guidance literature:

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol; 2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl trichloroacetimidate; With 4 A molecular sieve; In dichloromethane; for 2.5h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1071/CH03227

Reference yield: 73.0%

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol (727989-26-6) + 2,4,6-tri-O-acetyl-3-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl trichloroacetimidate (727989-22-2) → (1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-5-[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)]oxy-3-aza-2,7,9-trioxabicyclo[4.4.0]decane (727989-28-8)

Guidance literature:

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol; 2,4,6-tri-O-acetyl-3-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl trichloroacetimidate; With 4 A molecular sieve; In dichloromethane; for 2.5h;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -30 ℃; for 1h;

DOI:10.1071/CH03227

upstream raw materials:

(diethoxymethyl)benzene

(4R,5S,6R)-N-benzyloxycarbonyl-4,5-dihydroxy-6-hydroxymethyl-3,4,5,6=tetrahydro-2H-1,2-oxazine

Downstream raw materials:

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-5-[(tetra-O-acetyl-β-D-glucopyranosyl)-(1->3)-O-(tri-O-acetyl-β-D-glucopyranosyl)]oxy-3-aza-2,7,9-trioxabicyclo[4.4.0]decane

(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-5-(tetra-O-acetyl-β-D-glucopyranosyl)oxy-3-aza-2,7,9-trioxabicyclo[4.4.0]decane