(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Base Information

Chemical Name:(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine
CAS No.:122992-58-9
Molecular Formula:C₃₆H₄₁N₃O₉
Molecular Weight:659.736
Hs Code.:

(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

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

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

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

There total 1 articles about (4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine 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: 99.0%

: 100-39-0
benzyl bromide

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

: 122992-58-9
(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; 1.) 1h, 2.) 16 h;

Reference yield:

: 122992-58-9
(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 104616-13-9
6-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-levulinoyl-β-D-glucopyranosyluronato)-α-D-glucopyranosyl bromide

Guidance literature:: Multi-step reaction with 9 steps

1: acetic acid; H₂O / 16 h / Ambient temperature

2: pyridine; tetrahydrofuran / 27 h

3: N,N-dimethylaminopyridine / pyridine; tetrahydrofuran / 6 h / 0 °C

4: acetic acid; H₂O / 4 h

5: chromium(VI) oxide / acetone; aq. H₂SO₄ / 24 h / 0 °C

6: CH₂Cl₂

7: trifluoroacetic acid / 16 h / Ambient temperature

8: piperidine / tetrahydrofuran / 16 h / Ambient temperature

9: oxalyl bromide / CHCl₃; dimethylformamide / 2.5 h / Ambient temperature

With piperidine; chromium(VI) oxide; Oxalyl bromide; trifluoroacetic acid; dmap; In tetrahydrofuran; pyridine; dichloromethane; chloroform; sulfuric acid; water; acetic acid; N,N-dimethyl-formamide; acetone;

Reference yield:

: 122992-58-9
(4aR,6S,7R,8S,8aR)-6-((1R,2S,3R,4R,5R)-4-Azido-3-benzyloxy-6,8-dioxa-bicyclo[3.2.1]oct-2-yloxy)-7,8-bis-benzyloxy-2,2-dimethyl-hexahydro-pyrano[3,2-d][1,3]dioxine

: 104616-12-8
1,6-di-O-acetyl-2-azido-3-O-benzyl-2-deoxy-4-O-(methyl 2,3-di-O-benzyl-4-O-levulinyl-β-D-glucopyranosyluronate)-D-glucopyranose

Guidance literature:: Multi-step reaction with 7 steps

1: acetic acid; H₂O / 16 h / Ambient temperature

2: pyridine; tetrahydrofuran / 27 h

3: N,N-dimethylaminopyridine / pyridine; tetrahydrofuran / 6 h / 0 °C

4: acetic acid; H₂O / 4 h

5: chromium(VI) oxide / acetone; aq. H₂SO₄ / 24 h / 0 °C

6: CH₂Cl₂

7: trifluoroacetic acid / 16 h / Ambient temperature

With chromium(VI) oxide; trifluoroacetic acid; dmap; In tetrahydrofuran; pyridine; dichloromethane; sulfuric acid; water; acetic acid; acetone;