2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal

Base Information

• Chemical Name: 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal
• CAS No.: 20702-87-8
• Molecular Formula: C₁₄H₂₆O₇
• Molecular Weight: 306.356
• Mol file: 20702-87-8.mol

Synonyms:2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal

Chemical Property of 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal

There total 4 articles about 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal 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: 65.0%

4-O-(2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal → 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal (20702-87-8) + 4-O-(2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranosyl)-2,3-O-isopropylidene-aldehydo-L-threo-hex-4-enose dimethyl acetal + 4-O-(2,6-di-O-benzyl-4-deoxy-α-L-threo-hex-4-enopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-45-7)

Guidance literature:

With potassium tert-butylate; In N,N-dimethyl-formamide; at 20 ℃; for 24h;

DOI:10.1016/j.carres.2003.08.001

Reference yield: 17.0%

acetic anhydride (108-24-7) + (E)-4-O-(2-deoxy-3,4-O-isopropylidene-2-hydroxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (263845-19-8) → 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal (20702-87-8) + 4-O-(2-acetamido-2,4-dideoxy-6-O-trityl-β-D-xylo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal + 4-O-(2-acetamido-2,4-dideoxy-6-O-trityl-β-D-ribo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal + 4-O-(2-acetamido-2-deoxy-3,4-O-isopropylidene-6-O-trityl-β-D-talopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (263845-21-2)

Guidance literature:

(E)-4-O-(2-deoxy-3,4-O-isopropylidene-2-hydroxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal; With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃;

acetic anhydride; In methanol; at 20 ℃;

DOI:10.1080/07328300008544066

Reference yield:

4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-52-6) → 2,3-5,6-bis-O-isopropylidene-aldehydo-D-glucose dimethylacetal (20702-87-8) + 2-O-benzyl-5-C-hydroxy-3,4-O-isopropylidene-1,6-anhydro-β-L-talopyranose + 2-O-benzyl-5-C-hydroxy-3,4-O-isopropylidene-1,6-anhydro-β-D-galactopyranose

Guidance literature:

With triethylamine; In methanol; water; at 20 ℃; for 3h;

DOI:10.1016/j.carres.2003.08.001

upstream raw materials:

acetic anhydride

(E)-4-O-(2-deoxy-3,4-O-isopropylidene-2-hydroxyimino-6-O-trityl-β-D-lyxo-hexopyranosyl)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

4-O-[(5RS)-2-O-benzyl-3,4-O-isopropylidene-5-C-m-chlorobenzoyloxy-α-L-arabino-hexopyranosyl]-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Downstream raw materials:

O⁴-methyl-D-glucose

1,3-bis(2,3,5,6-di-O-isopropylidine-D-glucose dimethylacetal-4-yloxy)-2-propane-O-benzyloxime

Bis-{2-[(R)-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy]-ethyl}-amine

Bis-{2-[(R)-((4S,5R)-5-dimethoxymethyl-2,2-dimethyl-[1,3]dioxolan-4-yl)-((R)-2,2-dimethyl-[1,3]dioxolan-4-yl)-methoxy]-ethyl}-(2,4-dinitro-phenyl)-amine