(3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Base Information

• Chemical Name: (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate
• CAS No.: 4627-41-2
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.598

Synonyms:

Chemical Property of (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate

There total 11 articles about (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate 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: 100.0%

gentibiose (536-11-8,645-03-4,902-54-5,3031-35-4,4604-26-6,5340-95-4,5995-99-3,5996-00-9,13299-20-2,13299-21-3,15548-40-0,16750-26-8,16967-97-8,23339-29-9,24822-33-1,33428-65-8,34674-94-7,35867-21-1,37169-69-0,37169-72-5,38533-27-6,50271-70-0,65207-30-9,82729-73-5,95463-59-5,100427-99-4,100430-37-3,100483-14-5,102572-70-3,110658-40-7,123809-47-2,140461-60-5,143615-15-0) + acetic anhydride (108-24-7) → (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (4613-78-9,4627-41-2,23846-69-7,29873-67-4,33585-14-7,41545-70-4,54631-77-5,55700-65-7,57128-39-9,57128-42-4,58769-76-9,58769-77-0,66007-86-1,69685-27-4,72691-29-3,80735-84-8,80735-85-9,80735-86-0,96094-92-7,99528-77-5,103475-60-1,110270-63-8,123809-60-9,49587-35-1)

Guidance literature:

With pyridine; at 50 ℃;

DOI:10.1039/d1ob02317a

Reference yield: 68.0%

acetic anhydride (108-24-7) + 6-O-(2,3,4,6-tetra-O-acetyl-α,β-D-galactopyranosyl)-D-galactopyranose → 1,2,3,4-tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α,β-D-galactopyranosyl)-D-galactopyranose (4613-78-9,4627-41-2,23846-69-7,29873-67-4,33585-14-7,41545-70-4,49587-35-1,54631-77-5,55700-65-7,57128-39-9,57128-42-4,58769-76-9,58769-77-0,66007-86-1,69685-27-4,72691-29-3,80735-84-8,80735-85-9,80735-86-0,96094-92-7,99528-77-5,103475-60-1,110270-63-8,123809-60-9)

Guidance literature:

With pyridine; Ambient temperature;

DOI:10.1016/S0008-6215(00)80793-4

Reference yield: 59.0%

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate (74808-10-9) + 1,2,3,4-tetra-O-acetyl-D-glucopyranose (65620-65-7) → (3R,4S,5R,6R)-6-((((2R,3R,4S,5R,6R)-3,4,5-triacetoxy-6-(acetoxymethyl)tetrahydro-2H-pyran-2-yl)oxy)methyl)tetrahydro-2H-pyran-2,3,4,5-tetrayl tetraacetate (4613-78-9,4627-41-2,23846-69-7,29873-67-4,33585-14-7,41545-70-4,54631-77-5,55700-65-7,57128-39-9,57128-42-4,58769-76-9,58769-77-0,66007-86-1,69685-27-4,72691-29-3,80735-84-8,80735-85-9,80735-86-0,96094-92-7,99528-77-5,103475-60-1,110270-63-8,123809-60-9,49587-35-1)

Guidance literature:

O-(2,3,4,6-Tetra-O-acetyl-α-D-glucopyranosyl)trichloroacetimidate; 1,2,3,4-tetra-O-acetyl-D-glucopyranose; In dichloromethane; for 0.5h; Inert atmosphere; Molecular sieve;

With trimethylsilyl trifluoromethanesulfonate; In dichloromethane; at -25 - 20 ℃; for 24h; Inert atmosphere;

DOI:10.1016/j.tetlet.2013.10.042

upstream raw materials:

acetic anhydride

gentibiose

2,3,4,6-tetra-O-acetyl-d-glucopyranosyl trichloroacetimidate

1,2,3,4-tetra-O-acetyl-D-glucopyranose

Downstream raw materials:

O-(α-D-glucopyranosyl)-(1<*>6)-O-β-D-glucopyranosyl-(1<*>6)-N-(L-β-aspartyl)-α-D-glucopyranosylamine

O-(α-D-glucopyranosyl)-(1<*>6)-O-β-D-glucopyranosyl-(1<*>6)-N-(L-β-aspartyl)-β-D-glucopyranosylamine

O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-acel-β-D-glucopyranosyl)-(1<*>6)-(2,3,4-tri-O-acetyl-N-)O-ethyl-N-(O-ethyl-N-benzyloxycarbonyl-L-β-aspartyl)-β-D-glucopyranosylamine

O-(2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl)-(1<*>6)-O-(2,3,4-tri-O-acetyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-acetyl-N-(O-ethyl-N-benzyloxycarbonyl-L-β-aspartyl)-α-D-glucopyranosylamine

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