(2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol

Base Information

• Chemical Name: (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol
• CAS No.: 1233216-85-7
• Molecular Formula: C₄₁H₆₁N₃O₃Si
• Molecular Weight: 672.039

Synonyms:(2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol

Chemical Property of (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol

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Technology Process of (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol

There total 1 articles about (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-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: 99.0%

C25H43N3O3 (1057620-74-2) + tert-butylchlorodiphenylsilane (58479-61-1) → (2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol (1233216-85-7)

Guidance literature:

With triethylamine; In dichloromethane; at 0 - 20 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ml2000802

Reference yield: 85.0%

(2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol (1233216-85-7) → (4R,E)-2-azido-4-O-benzyl-1-O-tert-butyldiphenylsilyl-octadec-2-ene-1,4-diol (1233216-84-6)

Guidance literature:

With phthalimide; di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 20 ℃; for 1h;

DOI:10.1021/ol100934z

Reference yield: 72.0%

(2S,3S,4R)-2-azido-4-(benzyloxy)-1-(tert-butyldiphenylsilyloxy)octadecan-3-ol (1233216-85-7) → ((2S,3R,4R)-2-azido-4-(benzyloxy)-3-bromooctadecyloxy)(tert-butyl)diphenylsilane (1309668-37-8)

Guidance literature:

With carbon tetrabromide; triphenylphosphine; In dichloromethane; for 24h; Inert atmosphere;

DOI:10.1021/ml2000802

upstream raw materials:

C₂₅H₄₃N₃O₃

tert-butylchlorodiphenylsilane

Downstream raw materials:

(4R,E)-2-azido-4-O-benzyl-1-O-tert-butyldiphenylsilyl-octadec-2-ene-1,4-diol

(2S,3R,4S,5S,6R)-2-((2R,4R)-2-azido-4-(benzyloxy)octadecyloxy)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)tetrahydro-2H-pyran

((2S,3R,4R)-2-azido-4-(benzyloxy)-3-bromooctadecyloxy)(tert-butyl)diphenylsilane

(2R,4R)-2-amino-4-(benzyloxy)octadecan-1-ol

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