Beta-gentiobiose octaacetate

Base Information

• Chemical Name: Beta-gentiobiose octaacetate
• CAS No.: 4613-78-9
• Molecular Formula: C28H38O19
• Molecular Weight: 678.598
• Nikkaji Number: J1.503.161A
• Mol file: 4613-78-9.mol

Synonyms:Beta-gentiobiose octaacetate;4613-78-9;gentiobiose octaacetate;[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-[[(2R,3R,4S,5R,6S)-3,4,5,6-tetraacetyloxyoxan-2-yl]methoxy]oxan-2-yl]methyl acetate;BETA-GENTIOBIOSEOCTAACETATE;ss-Gentiobiose-octaacetat;SCHEMBL4876768;GNTLGGDVHFXGLI-QACPWNKNSA-N;MFCD00016917;[(2R,3R,4S,5R,6R)-3,4,5-TRIS(ACETYLOXY)-6-{[(2R,3R,4S,5R,6S)-3,4,5,6-TETRAKIS(ACETYLOXY)OXAN-2-YL]METHOXY}OXAN-2-YL]METHYL ACETATE

Chemical Property of Beta-gentiobiose octaacetate

Chemical Property:

• Melting Point: 191-195 °C
• Boiling Point: 661.384 °C at 760 mmHg
• Flash Point: 272.155 °C
• PSA: 238.09000
• Density: 1.37 g/cm³
• LogP: -0.83080
• XLogP3: 0.2
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 19
• Rotatable Bond Count: 20
• Exact Mass: 678.20072898
• Heavy Atom Count: 47
• Complexity: 1200

Purity/Quality:

98%Min ^*data from raw suppliers

b-Gentiobiose octaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)OCC1C(C(C(C(O1)OCC2C(C(C(C(O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Isomeric SMILES: CC(=O)OC[C@@H]1[C@H]([C@@H]([C@H]([C@@H](O1)OC[C@@H]2[C@H]([C@@H]([C@H]([C@@H](O2)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: β-D-Gentiobiose octaacetate (CAS# 4613-78-9) is a useful disaccharide building block used in the synthetic preparation of leptosin, and used in the glycosylation of alcohols.

Technology Process of Beta-gentiobiose octaacetate

There total 25 articles about Beta-gentiobiose octaacetate 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

O⁶-β-D-Glucopyranosyl-D-glucose

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

2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

Downstream raw materials:

phenyl-[O²,O³,O⁴-triacetyl-O⁶-(tetra-O-acetyl-β-D-glucopyranosyl)-β-D-glucopyranoside]

phenyl 2,3,4,2',3',4',6'-hepta-O-acetyl-1-thio-β-gentiobioside

allyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

2-methoxyethyl O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1<*>6)-2,3,4-tri-O-benzyl-β-D-glucopyranoside

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