3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose

Base Information

• Chemical Name: 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose
• CAS No.: 139631-37-1
• Molecular Formula: C₁₈H₂₁N₃O₇S
• Molecular Weight: 423.447

Synonyms:3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose

Chemical Property of 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose

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Technology Process of 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose

There total 2 articles about 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose 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: 79.0%

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) + thiophenol (108-98-5) → 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose (139631-37-1)

Guidance literature:

With boron trifluoride diethyl etherate; In dichloromethane; at 20 ℃; for 48h;

DOI:10.1016/j.tet.2012.10.058

Reference yield: 15.0%

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose (185114-94-7,155417-78-0) + thiophenol (108-98-5) → 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose (139631-37-1) + 3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-α-D-gluco-pyranose

Guidance literature:

With boron trifluoride diethyl etherate; In 1,2-dichloro-ethane; at 48 ℃; for 12h;

Reference yield: 100.0%

3-azido-1,3-dideoxy-1-(phenylsulfenyl)-2,4,6-tri-O-acetyl-β-D-gluco-pyranose (139631-37-1) → phenyl 3-azido-3-deoxy-1-thio-β-D-glucopyranoside (205676-46-6)

Guidance literature:

With sodium methylate; In methanol; for 17.5h; Ambient temperature;

DOI:10.1021/ja9910356

upstream raw materials:

1,2,4,6-Tetra-O-acetyl-3-azido-3-deoxy-α/β-gluco-hexopyranose

thiophenol

Downstream raw materials:

phenyl 3-azido-3-deoxy-1-thio-β-D-glucopyranoside

phenyl 3-azido-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

phenyl 3-azido-2-O-benzyl-4,6-O-benzylidene-3-deoxy-1-thio-β-D-glucopyranoside

phenyl 3-azido-2,6-di-O-benzyl-3-deoxy-1-thio-β-D-glycopyranoside

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