1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose

Base Information

• Chemical Name: 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose
• CAS No.: 132016-21-8
• Molecular Formula: C₁₃H₂₁NO₈
• Molecular Weight: 319.312

Synonyms:1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose

Chemical Property of 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose

Chemical Property:

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Technology Process of 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose

There total 7 articles about 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose 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: 62.0%

(1S,2S,3S,4R,5R)-4-Benzyloxy-2-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol (176389-14-3) → 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose (132016-21-8)

Guidance literature:

With ammonia; sodium; In tetrahydrofuran; at -78 ℃; for 1h;

DOI:10.1071/C96155

Reference yield:

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose (33208-46-7) → 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose (132016-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / butan-1-ol / 72 h / 110 °C

2: 62 percent / sodium, NH₃ / tetrahydrofuran / 1 h / -78 °C

With ammonia; sodium; In tetrahydrofuran; butan-1-ol;

DOI:10.1071/C96155

Reference yield:

(1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol (128573-02-4) → 1,6-anhydro-4-deoxy-4-<(1R,4R,5S,6S)-4,5,6-trihydroxy-3-(hydroxymethyl)cyclohex-2-enyl>amino-β-D-glucose (132016-21-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 50 percent / butan-1-ol / 72 h / 110 °C

2: 62 percent / sodium, NH₃ / tetrahydrofuran / 1 h / -78 °C

With ammonia; sodium; In tetrahydrofuran; butan-1-ol;

DOI:10.1071/C96155

upstream raw materials:

(1S,2S,3S,4R,5R)-4-Benzyloxy-2-((1R,4R,5S,6S)-4,5,6-tris-benzyloxy-3-benzyloxymethyl-cyclohex-2-enylamino)-6,8-dioxa-bicyclo[3.2.1]octan-3-ol

1,6:3,4-Dianhydro-2-O-benzyl-β-D-galactopyranose

(1R,2S,3S,4R)-1-amino-2,3,4-tri-O-benzyl-5-(benzyloxymethyl)-cyclohex-5-ene-2,3,4-triol

2-O-acetyl-1,6:3,4-dianhydro-β-D-galactopyranose

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