6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide

Base Information

• Chemical Name: 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide
• CAS No.: 246855-92-5
• Molecular Formula: C₃₀H₄₇NO₁₈
• Molecular Weight: 709.699

Synonyms:6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide

Chemical Property of 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide

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Technology Process of 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide

There total 5 articles about 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide 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: 66.0%

6-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid (246855-91-4) + p-aminophenyl-α-D-mannopyranoside (34213-86-0) → 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide (246855-92-5)

Guidance literature:

With diphenylphosphoranyl azide; triethylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃;

DOI:10.1016/S0968-0896(99)00099-1

Reference yield:

methyl 6-hydroxycaproate (4547-43-7) → 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide (246855-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / HgO; HgBr₂; MS 4A / CHCl₃ / 48 h / 20 °C

2: NaOMe / methanol / 3 h / 0 °C / pH 10

3: LiOH / methanol; H₂O / 1 h / pH 11

4: 66 percent / diphenylphosphoryl azide; Et₃N / dimethylformamide / 0 - 20 °C

With lithium hydroxide; diphenylphosphoranyl azide; sodium methylate; triethylamine; mercury dibromide; mercury(II) oxide; In methanol; chloroform; water; N,N-dimethyl-formamide; 1: Koeenigs-Knorr glycosylation / 2: Zemplen deacetylation / 3: Hydrolysis / 4: amidation;

DOI:10.1016/S0968-0896(99)00099-1

Reference yield:

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide (4753-07-5) → 6-[3,4-dihydroxy-6-hydroxymethyl-5-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid [4-(3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-phenyl]-amide (246855-92-5)

Guidance literature:

Multi-step reaction with 4 steps

1: 74 percent / HgO; HgBr₂; MS 4A / CHCl₃ / 48 h / 20 °C

2: NaOMe / methanol / 3 h / 0 °C / pH 10

3: LiOH / methanol; H₂O / 1 h / pH 11

4: 66 percent / diphenylphosphoryl azide; Et₃N / dimethylformamide / 0 - 20 °C

With lithium hydroxide; diphenylphosphoranyl azide; sodium methylate; triethylamine; mercury dibromide; mercury(II) oxide; In methanol; chloroform; water; N,N-dimethyl-formamide; 1: Koeenigs-Knorr glycosylation / 2: Zemplen deacetylation / 3: Hydrolysis / 4: amidation;

DOI:10.1016/S0968-0896(99)00099-1

upstream raw materials:

6-[(2R,3R,4R,5S,6R)-3,4-Dihydroxy-6-hydroxymethyl-5-((2S,3R,4S,5R,6R)-3,4,5-trihydroxy-6-hydroxymethyl-tetrahydro-pyran-2-yloxy)-tetrahydro-pyran-2-yloxy]-hexanoic acid

p-aminophenyl-α-D-mannopyranoside

methyl 6-hydroxycaproate

2,3,6,2',3',4',6'-hepta-O-acetyl-lactosyl bromide

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