(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

Base Information

• Chemical Name: (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
• CAS No.: 213591-31-2
• Molecular Formula: C₄₀H₅₁N₃O₁₆Si
• Molecular Weight: 857.941

Synonyms:(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

Chemical Property of (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

Chemical Property:

Purity/Quality:

Safty Information:

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Useful:

Technology Process of (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

There total 3 articles about (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 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: 92.0%

(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) + tert-butylchlorodiphenylsilane (58479-61-1) → (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)

Guidance literature:

With 1H-imidazole; In N,N-dimethyl-formamide; for 12h; Ambient temperature;

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

Reference yield: 76.0%

(2S,3R,4S,5S,6R)-2-(((2R,3S,4R,5R)-4-acetoxy-2-(acetoxymethyl)-5-azido-6-hydroxytetrahydro-2H-pyran-3-yl)oxy)-6-(acetoxymethyl)tetrahydro-2H-pyran-3,4,5-triyl triacetate + tert-butylchlorodiphenylsilane (58479-61-1) → (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)

Guidance literature:

With 1H-imidazole; dmap; In N,N-dimethyl-formamide; at 20 ℃; for 10h; Inert atmosphere;

DOI:10.1021/acs.orglett.8b00814

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,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)

Guidance literature:

Multi-step reaction with 2 steps

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

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

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

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

tert-butylchlorodiphenylsilane

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

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

(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

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