2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid

Base Information

• Chemical Name: 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid
• CAS No.: 562043-84-9
• Molecular Formula: C₃₀H₃₆O₁₅
• Molecular Weight: 636.607

Synonyms:2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid

Chemical Property of 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid

Chemical Property:

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Technology Process of 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid

There total 9 articles about 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid 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: 75.5%

O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid (562043-84-9)

Guidance literature:

With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; at 35 ℃; for 4h; Reagent/catalyst; Temperature;

Reference yield: 67.0%

O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1) + (2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)carbonic acid 2,2,2-trichloroethyl ester → 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid (562043-84-9)

Guidance literature:

at 120 - 130 ℃; for 3h;

DOI:10.1021/jf035445w

Reference yield: 59.0%

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) + O3-benzyl-O5,O6-(1-methylethylidene)-L-ascorbic acid (86404-07-1) → 2-O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-3-O-benzyl-5,6-O-isopropylidene-L-ascorbic acid (562043-84-9)

Guidance literature:

With potassium chloride; sodium hydrogencarbonate; In dichloromethane; at 40 ℃; for 48h;

DOI:10.2533/CHIMIA.2020.828

upstream raw materials:

O³-benzyl-O⁵,O⁶-(1-methylethylidene)-L-ascorbic acid

benzyl bromide

5,6-O-isopropylidene-L-ascorbic acid

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

2-O-β-D-glucopyranosyl L-ascorbic acid

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