3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose

Base Information

• Chemical Name: 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose
• CAS No.: 1346679-02-4
• Molecular Formula: C₂₃H₃₁NO₇
• Molecular Weight: 433.502
• Mol file: 1346679-02-4.mol

Synonyms:3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose

Chemical Property of 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose

There total 2 articles about 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose 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: 96.0%

3-benzyloxycarbonylamino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose (25791-21-3) + allyl bromide (106-95-6) → 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose (1346679-02-4)

Guidance literature:

3-benzyloxycarbonylamino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose; With sodium hydride; In tetrahydrofuran; at 0 ℃; for 0.166667h;

allyl bromide; With tetra-(n-butyl)ammonium iodide; In tetrahydrofuran; at 0 - 20 ℃; for 3.16667h;

DOI:10.1016/j.tetlet.2011.09.039

Reference yield:

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (21870-78-0) → 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose (1346679-02-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: water; triphenylphosphine / tetrahydrofuran / 30 h / 20 °C

2.1: sodium hydrogencarbonate / tetrahydrofuran; water / 0 - 25 °C

3.1: sodium hydride / tetrahydrofuran / 0.17 h / 0 °C

3.2: 3.17 h / 0 - 20 °C

With water; sodium hydride; sodium hydrogencarbonate; triphenylphosphine; In tetrahydrofuran; water; 1.1: Staudinger reduction;

DOI:10.1016/j.tetlet.2011.09.039

Reference yield: 90.0%

3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose (1346679-02-4) → 3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-α-D-allo-1,4-furanose (1346679-03-5)

Guidance literature:

With sulfuric acid; In methanol; water; at 0 - 30 ℃; regioselective reaction;

DOI:10.1016/j.tetlet.2011.09.039

upstream raw materials:

3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose

3-benzyloxycarbonylamino-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allo-1,4-furanose

allyl bromide

Downstream raw materials:

Allyl-((3aR,5R,6R,6aR)-2,2-dimethyl-5-vinyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl)-carbamic acid benzyl ester

3-[(allyl)(benzyloxycarbonyl)amino]-3-deoxy-1,2-O-isopropylidene-α-D-allo-1,4-furanose

C₁₄H₁₇NO₄

(8R,8aS)-8-hydroxy-8,8a-dihydro-1H-oxazolo[3,4-a]pyridin-3(5H)-one