allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside

Base Information

• Chemical Name: allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside
• CAS No.: 250127-82-3
• Molecular Formula: C₆₄H₆₆O₁₁
• Molecular Weight: 1011.22

Synonyms:allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside

Chemical Property of allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside

Chemical Property:

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Technology Process of allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside

There total 2 articles about allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside 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: 81.0%

prop-2-ynyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside (214333-99-0) → allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside (250127-82-3)

Guidance literature:

With potassium tert-butylate; In methanol; dimethyl sulfoxide; at 20 ℃; for 1.5h;

DOI:10.1016/S0040-4020(99)00631-6

Reference yield:

benzyl bromide (100-39-0) → allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside (250127-82-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 78 percent / NaH / dimethylformamide / 2 h / 20 °C

2: 81 percent / KOt-Bu / dimethylsulfoxide; methanol / 1.5 h / 20 °C

With potassium tert-butylate; sodium hydride; In methanol; dimethyl sulfoxide; N,N-dimethyl-formamide; 1: Substitution / 2: Isomerization;

DOI:10.1016/S0040-4020(99)00631-6

Reference yield: 97.0%

allenyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside (250127-82-3) → 2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose (115988-74-4)

Guidance literature:

With osmium(VIII) oxide; N-methyl-2-indolinone; In acetone; at 20 ℃; for 15h;

DOI:10.1016/S0040-4020(99)00631-6

upstream raw materials:

prop-2-ynyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-galactopyranosyl)-2',3',6'-tri-O-benzyl-β-D-glucopyranoside

benzyl bromide

Downstream raw materials:

2,3,6-tri-O-benzyl-4-O-(2′,3′,4′,6′-tetra-O-benzyl-β-D-galactopyranosyl)-D-glucopyranose

1-[(2R,3R,4S,5R,6R)-3,4-Bis-benzyloxy-6-benzyloxymethyl-5-((2S,3R,4S,5S,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-propan-2-one

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