(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

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Chemical Name:(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol
CAS No.:135415-93-9
Molecular Formula:C₃₃H₃₅N₃O₉
Molecular Weight:617.656
Hs Code.:

Synonyms:(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

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Chemical Property of (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

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Technology Process of (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

There total 2 articles about (1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-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: 90.0%

: 99541-22-7
O-(2,3-di-O-benzyl-4,6-O-benzylidene-β-D-glucopyranosyl)-(1->4)-1,6:2,3-dianhydro-β-D-mannopyranose

: 135415-93-9
(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: With sodium azide; In water; N,N-dimethyl-formamide; for 16h; Reflux;

Reference yield:

: 99571-46-7
2',3'-di-O-benzyl derivative of 1,6-anhydro-4',6'-O-benzylidenecellobiose

: 135415-93-9
(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 91 percent Turnov_. / 1-tosylimidazole, sodium methoxide / CHCl₃; hexane / 5.5 h / Heating

2: sodium azide, ammonium chloride / dimethylformamide; H₂O / 37 h / 100 °C

With sodium azide; ammonium chloride; sodium methylate; N-tosylimidazole; In hexane; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1016/S0008-6215(00)90458-0

Reference yield:

: 135415-93-9
(1R,2S,3R,4R,5R)-4-Azido-2-((4aR,6S,7R,8S,8aR)-7,8-bis-benzyloxy-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

: 99541-26-1
O-(methyl 2,3-di-O-benzyl-β-D-glucopyranosyluronate)-(1->4)-3-O-acetyl-1,6-anhydro-2-azido-2-deoxy-β-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: pyridine / CH₂Cl₂ / 1.) 0-5 deg C 2.) r.t., 3 h

2: 94 percent / cupric chloride dihydrate / various solvent(s); ethanol / 1 h / Heating

3: pyridine / 4 h / 85 °C

4: pyridine / 1.) 0-5 deg C 2.) r.t., 30 min

5: Jones's reagent (4M chromium trioxide) / acetone / 1.) 0-5 deg C 2.) r.t., 50 min

6: CH₂Cl₂; diethyl ether

7: 71 percent / thiourea / ethanol / 6 h / Heating

With pyridine; chromium(VI) oxide; thiourea; copper dichloride; In diethyl ether; ethanol; dichloromethane; acetone;
DOI:10.1016/S0008-6215(00)90458-0