(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

Base Information

Chemical Name:(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
CAS No.:727989-28-8
Molecular Formula:C₄₆H₅₅NO₂₃
Molecular Weight:989.936
Hs Code.:

(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

Synonyms:(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

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Chemical Property of (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

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Technology Process of (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

There total 5 articles about (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 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: 73.0%

: 727989-26-6
(1R,5R,6S,8R)-3-benzyloxycarbonyl-8-phenyl-3-aza-2,7,9-trioxabicyclo[4.4.0]decan-5-ol

: 727989-22-2
2,4,6-tri-O-acetyl-3-O-(tetra-O-acetyl-β-D-glucopyranosyl)-α-D-glucopyranosyl trichloroacetimidate

: 727989-28-8
(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

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

Reference yield:

: 2,4,6-tri-O-acetyl-3-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-α,β-D-glucopyranose

: 727989-28-8
(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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 84 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h

2.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h

2.2: 73 percent / TMSOTf / CH₂Cl₂ / 1 h / -30 °C

With 4 A molecular sieve; 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;
DOI:10.1071/CH03227

Reference yield:

: 774-48-1
(diethoxymethyl)benzene

: 727989-28-8
(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

Guidance literature:: Multi-step reaction with 2 steps

1.1: 81 percent / camphorsulfonic acid / CHCl₃ / 1 h / Heating

2.1: molecular sieves 4 Angstroem / CH₂Cl₂ / 2.5 h

2.2: 73 percent / TMSOTf / CH₂Cl₂ / 1 h / -30 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; In dichloromethane; chloroform;
DOI:10.1071/CH03227