(2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol

Base Information

• Chemical Name: (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol
• CAS No.: 303752-86-5
• Molecular Formula: C₄₅H₆₃N₃O₈
• Molecular Weight: 774.011
• Mol file: 303752-86-5.mol

Synonyms:(2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol

Chemical Property of (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol

There total 15 articles about (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-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: 89.0%

1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol (303752-91-2) → (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol (303752-86-5)

Guidance literature:

With TMGN₃; In N,N-dimethyl-formamide; at 20 ℃; for 48h;

DOI:10.1016/S0008-6215(00)00092-6

Reference yield: 49.0%

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol (117168-59-9) + O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate (303752-87-6) → (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol (303752-86-5)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; In tetrahydrofuran; at -20 ℃; for 0.5h;

DOI:10.1016/S0008-6215(00)00092-6

Reference yield: 47.0%

(R)-1-((2R,3R)-3-((((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)methyl)oxiran-2-yl)pentadecan-1-ol → C45H63N3O8 + (2S,3S,4R)-2-azido-1-(((2S,4aS,6S,7R,8S,8aR)-7,8-bis(benzyloxy)-2-phenylhexahydropyrano[3,2-d][1,3]dioxin-6-yl)oxy)octadecane-3,4-diol (303752-86-5)

Guidance literature:

With sodium azide; ammonium chloride; In methanol; water; at 100 ℃; for 24h; Inert atmosphere; Sealed tube;

DOI:10.1021/acs.jmedchem.1c00881

upstream raw materials:

(2S,3S,4R)-2-azido-1,3,4-octadecanetriol

O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl) trichloroacetimidate

1-O-(2,3-di-O-benzyl-4,6-O-benzylidene-α-D-galactopyranosyl)-2-O-methanesulfonyl-D-arabino-1,2,3,4-octadecantetrol

benzyl bromide

Downstream raw materials:

2-azido-3,4-di-O-benzyl-1-O-(2,3-di-O-benzyloxyl-4,6-O-benzyllidene-α-D-galactopyranosyl)-D-ribooctadecane-1,3,4-triol