(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

Base Information

Chemical Name:(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol
CAS No.:180196-24-1
Molecular Formula:C₃₀H₃₆ClN₃O₅
Molecular Weight:554.086
Hs Code.:

Synonyms:(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

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Chemical Property of (4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

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Technology Process of (4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

There total 3 articles about (4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol 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:

: 18039-26-4,20787-16-0,20787-21-7,77943-32-9,77943-33-0,89615-43-0,89615-44-1,90899-55-1
2,3,4-tri-O-benzyl-D-arabinopyranose

: 180196-24-1
(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

Guidance literature:: Multi-step reaction with 3 steps

1: 1.) potassium bis(trimethylsilil)amide / 1.) THF, toluene, 0 deg C, 30 min, 2.) THF, -78 -> 0 deg C, 6 h

2: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

3: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

With osmium(VIII) oxide; hydrogen azide; potassium hexamethylsilazane; sodium hydrogensulfite; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In benzene;
DOI:10.1021/jo960609b

Reference yield:

: 154813-30-6
(Z)-(2R,3S,4R)-2,3,4-tris(benzyloxy)-9-chloro-5-nonen-1-ol

: 180196-24-1
(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

Guidance literature:: Multi-step reaction with 2 steps

1: 84 percent / hydrazoic acid, PPh₃, diethyl azodicarboxylate / benzene / 0.42 h / Ambient temperature

2: 1.) 4percent OsO₄, N-methylmorfoline N-oxide, 2.) 10percent sodium bisulfite / 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min

With osmium(VIII) oxide; hydrogen azide; sodium hydrogensulfite; 4-methylmorpholine N-oxide; triphenylphosphine; diethylazodicarboxylate; In benzene;
DOI:10.1021/jo960609b

Reference yield:

: 154813-31-7
(2R,3S,4R,5Z)-1-azido-2,3,4-tri(benzyloxy)-9-chloro-5-nonene

: 180196-24-1
(4R,5R,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

: 180323-14-2
(4S,5S,6R,7R,8R)-9-Azido-6,7,8-tris-benzyloxy-1-chloro-nonane-4,5-diol

Guidance literature:: With osmium(VIII) oxide; sodium hydrogensulfite; 4-methylmorpholine N-oxide; Yield given. Multistep reaction. Yields of byproduct given; 1.) THF, t-BuOH, H₂O, 72 h, 2.) 30 min;
DOI:10.1021/jo960609b