3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol

Base Information

• Chemical Name: 3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol
• CAS No.: 443916-29-8
• Molecular Formula: C29H29N3O4
• Molecular Weight: 483.57

Synonyms:3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol

Chemical Property of 3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol

There total 4 articles about 3,7-Anhydro-4-azido-1,2,4-trideoxy-5,6,8-tris-O-(phenylmethyl)-D-glycero-D-gulo-oct-1-ynitol 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: 90.0%

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol (443916-28-7) → 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol (443916-29-8)

Guidance literature:

With sodium hydroxide; In methanol; dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/jo020054m

Reference yield:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose → 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol (443916-29-8)

Guidance literature:

Multi-step reaction with 4 steps

1: pyridinium chlorochromate

2: CeCl₃; BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

3: 93 percent / Et₃SiH; BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -10 °C

4: 90 percent / aq. NaOH / CH₂Cl₂; methanol / 1 h / 20 °C

With triethylsilane; sodium hydroxide; n-butyllithium; cerium(III) chloride; boron trifluoride diethyl etherate; pyridinium chlorochromate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo020054m

Reference yield:

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lactone (175981-90-5) → 3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol (443916-29-8)

Guidance literature:

Multi-step reaction with 3 steps

1: CeCl₃; BuLi / tetrahydrofuran; hexane / 2 h / -78 °C

2: 93 percent / Et₃SiH; BF₃*Et₂O / acetonitrile; CH₂Cl₂ / 1 h / -10 °C

3: 90 percent / aq. NaOH / CH₂Cl₂; methanol / 1 h / 20 °C

With triethylsilane; sodium hydroxide; n-butyllithium; cerium(III) chloride; boron trifluoride diethyl etherate; In tetrahydrofuran; methanol; hexane; dichloromethane; acetonitrile;

DOI:10.1021/jo020054m

upstream raw materials:

3,7-anhydro-4-azido-5,6,8-tri-O-benzyl-1,2,4-trideoxy-D-glycero-D-gulo-oct-1-ynitol

2-azido-3,4,6-tri-O-benzyl-2-deoxy-D-glucono-1,5-lactone

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