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

Base Information

• Chemical Name: 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
• CAS No.: 639807-45-7
• Molecular Formula: C₃₄H₄₆O₁₁
• Molecular Weight: 630.733

Synonyms: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

Chemical Property of 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

Chemical Property:

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Technology Process of 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

There total 1 articles about 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 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: 96.0%

diiodomethane (75-11-6) + 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) → 4-O-{(1R,3R,4R,5S,6R)-4-(benzyloxy)-1-[(benzyloxy)methyl]-2-oxabicyclo[4.1.0]heptan-3-yl}-2,5:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

Guidance literature:

With diethylzinc; In diethyl ether; hexane; at 40 ℃; for 2h;

DOI:10.1016/j.tet.2004.03.018

Reference yield: 67.0%

methanol (67-56-1) + 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) → (5R)-2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal (639807-46-8)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; at 0 - 20 ℃; for 3h;

DOI:10.1016/j.carres.2003.08.001

Downstream raw materials:

(5R)-2,6-di-O-benzyl-5-C-methoxy-β-D-galactopyranosyl-(1->4)-2,3:5,6-di-O-isopropylidene-aldehydo-D-glucose dimethyl acetal

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