ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

Base Information

• Chemical Name: ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate
• CAS No.: 729596-18-3
• Molecular Formula: C₁₉H₂₅N₃O₇
• Molecular Weight: 407.423
• Mol file: 729596-18-3.mol

Synonyms:ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

Chemical Property of ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate

There total 3 articles about ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate 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: 81.7%

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ6-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester (729596-17-2) → ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate (729596-18-3)

Guidance literature:

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester; With sodium azide; In water; acetone; at 0 - 25 ℃; for 2h;

With sulfuric acid; In diethyl ether; water; at 25 ℃; for 6h;

DOI:10.1021/jo049509t

Reference yield:

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate (108788-49-4) → ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate (729596-18-3)

Guidance literature:

Multi-step reaction with 3 steps

1.1: K₃Fe(CN)6; K₂CO₃; (DHQD)2PHAL / potassium osmate; methanesulfonamide / 2-methyl-propan-2-ol; H₂O / 24 h / 0 °C

2.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

2.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

3.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

3.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

With pyridine; thionyl chloride; sodium azide; potassium carbonate; 1,4-bis(9-O-dihydroquinidine)phthalazine; potassium hexacyanoferrate(III); potassium osmate(VI); methanesulfonamide; In dichloromethane; water; acetone; tert-butyl alcohol; 1.1: Sharpless asymmetric dihydroxylation;

DOI:10.1021/jo049509t

Reference yield:

ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate (729596-15-0) → ethyl 6-azido-6-deoxy-3-O-benzyl-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranuronate (729596-18-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: pyridine; thionyl chloride / CH₂Cl₂ / 0.33 h / 0 °C

1.2: 86 percent / NaIO₄ / RuCl₃*3H₂O / acetonitrile; H₂O / 0.17 h / 0 °C

2.1: NaN₃ / acetone; H₂O / 2 h / 0 - 25 °C

2.2: 81.7 percent / H₂SO₄ / diethyl ether; H₂O / 6 h / 25 °C

With pyridine; thionyl chloride; sodium azide; In dichloromethane; water; acetone;

DOI:10.1021/jo049509t

upstream raw materials:

(4R,5S)-5-((3aR,5S,6S,6aR)-6-Benzyloxy-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-5-yl)-2,2-dioxo-2λ⁶-[1,3,2]dioxathiolane-4-carboxylic acid ethyl ester

ethyl (E)-[3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-α-D-gluco]-heptofuran-5-en-uronate

ethyl 3-O-benzyl-1,2-O-isopropylidene-β-L-glycero-D-gluco-heptofuranuronate

Downstream raw materials:

3,5,7-tri-O-acetyl-6-(N-benzyloxycarbonylamino)-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-heptofuranose

6-benzyloxycarbonylamino-6-deoxy-1,2-O-isopropylidene-α-D-glycero-D-gluco-hepto-1,4-furanose