(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Base Information

Chemical Name:(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid
CAS No.:184643-34-3
Molecular Formula:C₂₃H₃₁N₅O₉
Molecular Weight:521.527
Hs Code.:

Synonyms:(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

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Chemical Property of (4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

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Technology Process of (4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

There total 3 articles about (4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid 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: 62.0%

: 184643-33-2
(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid ethyl ester

: 184643-34-3
(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Guidance literature:: With lithium hydroxide; In methanol; water; for 12h; Ambient temperature;
DOI:10.1021/jo9614856

Reference yield:

: 184643-32-1
(3aR,4R,7aR)-2-(5-Benzyloxycarbonylamino-pentyl)-4-((1S,2R)-1,2,3-triacetoxy-propyl)-3a,7a-dihydro-4H-pyrano[3,4-d]oxazole-6-carboxylic acid ethyl ester

: 184643-34-3
(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 81 percent / Me₃SiN₃ / 2-methyl-propan-2-ol / 4 h / 80 °C

2: 62 percent / LiOH*H₂O / methanol; H₂O / 12 h / Ambient temperature

With lithium hydroxide; trimethylsilylazide; In methanol; water; tert-butyl alcohol;
DOI:10.1021/jo9614856

Reference yield:

: 184643-31-0
(4S,5R,6R)-2,4-Diacetoxy-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1S,2R)-1,2,3-triacetoxy-propyl)-tetrahydro-pyran-2-carboxylic acid ethyl ester

: 184643-34-3
(4S,5R,6R)-4-Azido-5-(6-benzyloxycarbonylamino-hexanoylamino)-6-((1R,2R)-1,2,3-trihydroxy-propyl)-5,6-dihydro-4H-pyran-2-carboxylic acid

Guidance literature:: Multi-step reaction with 3 steps

1: 73 percent / CF₃SO₃SiMe₃ / acetonitrile / 2.5 h / 50 °C

2: 81 percent / Me₃SiN₃ / 2-methyl-propan-2-ol / 4 h / 80 °C

3: 62 percent / LiOH*H₂O / methanol; H₂O / 12 h / Ambient temperature

With lithium hydroxide; trimethylsilyl trifluoromethanesulfonate; trimethylsilylazide; In methanol; water; acetonitrile; tert-butyl alcohol;
DOI:10.1021/jo9614856