(3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose

Base Information

• Chemical Name: (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose
• CAS No.: 74925-18-1
• Molecular Formula: C₁₂H₁₉ClO₅
• Molecular Weight: 278.733
• Mol file: 74925-18-1.mol

Synonyms:(3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose

Chemical Property of (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose

There total 5 articles about (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-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: 57.0%

O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate (16667-96-2,28251-91-4,64481-59-0,64481-60-3,77454-06-9,77454-07-0,100638-80-0,100638-81-1,143037-49-4) → (3aR,5R,6S,6aS)-6-Chloro-5-(2,2-dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[2,3-d][1,3]dioxole (32785-94-7,32785-97-0,74925-18-1)

Guidance literature:

With sulfuryl dichloride; In acetonitrile; 1.) 0 deg C, 1 h, 2.) 7 h, room temperature;

DOI:10.1016/0040-4039(88)85083-4

Reference yield: 53.7%

1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → 3-deoxy-1,2:5,6-di-O-isopropylidene-α-D-erythro-hex-3-enofuranose (2774-28-9) + (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose (74925-18-1) + 6-chloro-O1,O2;O3,O5-diisopropylidene-α-D-6-deoxy-glucofuranose (19685-14-4)

Guidance literature:

With 1H-imidazole; N-chloro-succinimide; triphenylphosphine; In chlorobenzene; for 3h; Heating;

DOI:10.1016/0008-6215(92)84042-Q

Reference yield: 31.0%

Benzotrichlorid (98-07-7) + 1,2:5,6-di-O-isopropylidene-α-D-glucofuranose (582-52-5) → benzylidene dichloride (98-87-3) + (3R)-3-chloro-3-deoxy-1,2:5,6-di-O-isoproplylidene-α-D-allofuranose (74925-18-1)

Guidance literature:

With TOP; phenylsilane; In neat (no solvent); at 100 ℃; for 24h; Inert atmosphere;

DOI:10.1021/acs.joc.9b00741

upstream raw materials:

3-trifluoromethanesulphonate-1,2:3,4-di-O-isopropylidene-α-D-glucofuranose

O-[(3aR,5R,6S,6aR)-5-(2,2-dimethyl-1,3-dioxolan-4-yl)-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-6-yl] methylsulfanylmethanethioate

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

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