(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Base Information

• Chemical Name: (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol
• CAS No.: 213591-32-3
• Molecular Formula: C₂₈H₃₉N₃O₁₀Si
• Molecular Weight: 605.717

Synonyms:(2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property of (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

Chemical Property:

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Technology Process of (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol

There total 3 articles about (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol 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: 98.0%

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-((tertbutyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (213591-31-2) → (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (213591-32-3)

Guidance literature:

With sodium methylate; In methanol; for 3h; Ambient temperature;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1887::aid-ejoc1887>3.0.co;2-i

Reference yield:

3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate (68733-14-2) → (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (213591-32-3)

Guidance literature:

Multi-step reaction with 3 steps

1: CaCO₃ / acetone; H₂O / 48 h / Ambient temperature

2: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

3: 98 percent / NaOMe / methanol / 3 h / Ambient temperature

With 1H-imidazole; sodium methylate; calcium carbonate; In methanol; water; N,N-dimethyl-formamide; acetone;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1887::aid-ejoc1887>3.0.co;2-i

Reference yield:

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2Hpyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate (94715-70-5) → (2S,3R,4S,5R,6R)-2-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-6-hydroxymethyl-tetrahydro-pyran-3,4,5-triol (213591-32-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 92 percent / imidazole / dimethylformamide / 12 h / Ambient temperature

2: 98 percent / NaOMe / methanol / 3 h / Ambient temperature

With 1H-imidazole; sodium methylate; In methanol; N,N-dimethyl-formamide;

DOI:10.1002/(sici)1099-0690(199809)1998:9<1887::aid-ejoc1887>3.0.co;2-i

upstream raw materials:

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R,6S)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-((tertbutyldiphenylsilyl)oxy)tetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

3,6-di-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)-2-azido-2-deoxy-α-D-glucopyranosyl nitrate

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2Hpyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate

Downstream raw materials:

tert-butyldiphenylsilyl 2,6-di-O-benzyl-3,4-O-isopropylidene-β-D-galactopyranosyl-(1->4)-2-azido-3,6-di-O-benzyl-2-deoxy-β-D-glucopyranoside

2,2,2-Trichloro-acetimidic acid (2R,3R,4R,5S,6R)-3-azido-4-benzyloxy-5-((3aS,4R,6S,7R,7aS)-7-benzyloxy-4-benzyloxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-6-yloxy)-6-benzyloxymethyl-tetrahydro-pyran-2-yl ester

(3aS,4R,6S,7R,7aR)-6-[(2R,3S,4R,5R,6S)-5-Azido-6-(tert-butyl-diphenyl-silanyloxy)-4-hydroxy-2-hydroxymethyl-tetrahydro-pyran-3-yloxy]-4-hydroxymethyl-2,2-dimethyl-tetrahydro-[1,3]dioxolo[4,5-c]pyran-7-ol

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