(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Base Information

Chemical Name:(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol
CAS No.:143921-43-1
Molecular Formula:C₄₁H₄₃N₃O₉
Molecular Weight:721.807
Hs Code.:

(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Synonyms:(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-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-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-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-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

There total 9 articles about (1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-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: 65.0%

: 143921-50-0
(1R,2S,4S,5R,6R)-5-((3aS,4R,6S,7R,7aS)-7-Benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-3,8,9-trioxa-tricyclo[4.2.1.0^2,4]nonane

: 143921-43-1
(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: With sodium azide; cesium fluoride; In N,N-dimethyl-formamide; at 110 ℃; for 48h;
DOI:10.1246/cl.1992.1413

Reference yield:

: 100-39-0
benzyl bromide

: 143921-43-1
(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: Multi-step reaction with 2 steps

1: 89 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide

2: 65 percent / NaN₃, CsF / dimethylformamide / 48 h / 110 °C

With barium dihydroxide; sodium azide; cesium fluoride; barium(II) oxide; In N,N-dimethyl-formamide;
DOI:10.1246/cl.1992.1413

Reference yield:

: 76-83-5
trityl chloride

: 143921-43-1
(1R,2S,3R,4R,5R)-4-Azido-2-((3aS,4R,6S,7R,7aS)-7-benzyloxy-2,2-dimethyl-4-trityloxymethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) pyridine, 2.) Ac₂O, pyridine, 3.) NaOMe

2: 10-camphorsulfonic acid / dimethylformamide / 6 h / 60 °C / 20 Torr

3: dimethylaminopyridine (DMAP), pyridine / 18 h / 25 °C

4: 87 percent / 1 M aq. NaOH / tetrahydrofuran; methanol / 15 h / 25 °C

5: 89 percent / BaO, Ba(OH)2*8H₂O / dimethylformamide

6: 65 percent / NaN₃, CsF / dimethylformamide / 48 h / 110 °C

With pyridine; dmap; barium dihydroxide; sodium hydroxide; sodium azide; (1S)-10-camphorsulfonic acid; sodium methylate; acetic anhydride; cesium fluoride; barium(II) oxide; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;
DOI:10.1246/cl.1992.1413