3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose

Base Information

• Chemical Name: 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose
• CAS No.: 21870-78-0
• Molecular Formula: C12H19N3O5
• Molecular Weight: 285.3
• Mol file: 21870-78-0.mol

Synonyms:3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose

Chemical Property of 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose

There total 8 articles about 3-Azido-3-deoxy-1,2:5,6-di-O-isopropylidene-alpha-D-allofuranose 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: 72.0%

1,2:5,6-di-O-isopropylidene-3-O-(N-imidazole-1-sulfonyl)-α-D-glucofuranose (80667-81-8) → 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (21870-78-0) + 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

With sodium azide; tetrabutylammomium bromide; In dimethyl sulfoxide; at 20 - 80 ℃; for 10.5h;

DOI:10.1007/s00726-016-2346-5

Reference yield: 62.0%

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose (55951-93-4) → 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (21870-78-0) + 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

With tetramethylguanidinum azide; In N,N-dimethyl-formamide; at 25 ℃; for 6h;

DOI:10.1016/0008-6215(91)80125-7

Reference yield: 48.0%

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose (55951-93-4) → 3-azido-3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-allofuranose (21870-78-0) + 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9)

Guidance literature:

With sodium azide; In N,N-dimethyl-formamide; at 50 ℃; for 24h;

DOI:10.1080/07328309708006508

upstream raw materials:

1,2:5,6-di-O-isopropylidene-3-O-triflyl-α-D-glucofuranose

2,2,2-Trifluoro-1,1-diphenyl-ethanesulfonic acid (3aR,5R,6S,6aR)-5-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxol-6-yl ester

(1,2;5,6-Di-O-isopropyliden-α-D-glucofuranos-3-yloxy)phosphonium-azid

1,2:5,6-di-O-isopropylidene-3-O-tosyl-α-D-glucofuranoside

Downstream raw materials:

C₃₀H₃₄NO₅P

3-azido-3-deoxy-1,2-O-isopropylidene-α-D-ribofuranose

(2S,3S,4R,5R) 3-azido-4-hydroxy-5-(6-[3-iodobenzylamino]-purin-9-yl)-tetrahydro-furan-2-carboxylic acid methylamide

3-amino-5-(6-(3-iodobenzylamino)purin-9-yl)-4-t-butyldimethylsiloxy-tetrahydro-furan-2-carboxylic acid methyl amide