N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide

Base Information

• Chemical Name: N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide
• CAS No.: 77396-74-8
• Molecular Formula: C₃₈H₄₇NO₁₁
• Molecular Weight: 693.791

Synonyms:

Chemical Property of N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide

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Technology Process of N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide

There total 4 articles about N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide 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:

Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid (58700-48-4) → N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide (77396-74-8)

Guidance literature:

Multi-step reaction with 2 steps

1: NaOMe / methanol

2: toluene-p-sulphonic acid / 3 h / Ambient temperature

With sodium methylate; toluene-4-sulfonic acid; In methanol;

DOI:10.1039/P19810000326

Reference yield:

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside (55287-49-5) → N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide (77396-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: HgBr₂, activated molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 36 h / 80 °C

2: NaOMe / methanol

3: toluene-p-sulphonic acid / 3 h / Ambient temperature

With 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; mercury dibromide; In methanol; 1,2-dichloro-ethane;

DOI:10.1039/P19810000326

Reference yield:

1-bromo-1-deoxy-2,3,4,6-tetra-O-acetyl-a-D-galactopyranoside (3068-32-4) → N-[(2S,3R,4R,5S,6R)-2,4-Bis-benzyloxy-6-benzyloxymethyl-5-((3aS,4R,6S,7R,7aR)-7-hydroxy-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-tetrahydro-pyran-3-yl]-acetamide (77396-74-8)

Guidance literature:

Multi-step reaction with 3 steps

1: HgBr₂, activated molecular sieves (4 Angstroem) / 1,2-dichloro-ethane / 36 h / 80 °C

2: NaOMe / methanol

3: toluene-p-sulphonic acid / 3 h / Ambient temperature

With 4 A molecular sieve; sodium methylate; toluene-4-sulfonic acid; mercury dibromide; In methanol; 1,2-dichloro-ethane;

DOI:10.1039/P19810000326

upstream raw materials:

Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(β-D-galactopyranosyl)-α-D-glucopyranosid

acetone

Benzyl-2-acetamido-3,6-di-O-benzyl-2-desoxy-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-α-D-glucopyranosid

benzyl 2-acetamido-3,6-di-O-benzyl-2-deoxy-α-D-glucopyranoside

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