benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Base Information

• Chemical Name: benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS No.: 104731-78-4
• Molecular Formula: C₃₀H₄₀O₁₄
• Molecular Weight: 624.639

Synonyms:benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property of benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

Chemical Property:

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Technology Process of benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

There total 1 articles about benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 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: 87.1%

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) + 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (572-09-8) → benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (104731-78-4)

Guidance literature:

With mercury(II) cyanide; In acetonitrile;

DOI:10.1016/S0008-6215(00)90396-3

Reference yield: 72.7%

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (104731-78-4) + benzyl chloride (100-44-7) → benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (104731-82-0)

Guidance literature:

With potassium hydroxide; at 130 - 140 ℃; for 2h;

DOI:10.1016/S0008-6215(00)90396-3

Reference yield:

benzyl O-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (104731-78-4) → Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-[(3aR,4S,6S,7S,7aR)-4-(bromo-phenyl-methoxy)-2,2,6-trimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-yloxy]-tetrahydro-pyran-3-yl ester

Guidance literature:

With Bromotrichloromethane; In tetrachloromethane; Irradiation;

DOI:10.1016/S0040-4039(01)80784-X

upstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

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

Downstream raw materials:

benzyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl O-(2,4-di-O-benzyl-3-O-methyl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl O-(2,3,4-tri-O-benzyl-β-D-glucopyranosyl)-(1<*>4)-α-L-rhamnopyranoside

benzyl O-(2,3,4-tri-O-benzyl-6-O-trityl-β-D-glucopyranosyl)-(1<*>4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

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