Acetyl 6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose

Base Information

• Chemical Name: Acetyl 6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose
• CAS No.: 123809-60-9
• Molecular Formula: C28H38O19
• Molecular Weight: 678.59
• Mol file: 123809-60-9.mol

Synonyms:[(3R,4S,5R,6S)-3,4,5-Triacetoxy-6-[[(3R,4S,5R,6S)-3,4,5,6-tetraacetoxytetrahydropyran-2-yl]methoxy]tetrahydropyran-2-yl]methyl acetate;

Chemical Property of Acetyl 6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 193 °C
• Refractive Index: 1.507
• Boiling Point: 661.384 °C at 760 mmHg
• Flash Point: 272.155 °C
• PSA: 238.09000
• Density: 1.37 g/cm³
• LogP: -0.83080
• Solubility.: Dichloromethane

Purity/Quality:

99% ^*data from raw suppliers

Acetyl6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Acetyl 6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose

There total 11 articles about Acetyl 6-O-(2,3,4,6-Tetra-O-acetyl-α-D-mannopyranosyl)-2,3,4-tri-O-acetyl-D-mannopyrannose 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:

tert-butyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside

(-)-menthyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside

(+)-menthyl 6-O-[4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside

m-formyl-p-hydroxy-benzyl-β-D-glucopyranosyl-(1→6)-1-thio-β-D-glucopyranoside

Refernces

• 1、 Karimov, Rashad R.,Tan, Derek S.,Gin, David Y.. "Rapid assembly of the doubly-branched pentasaccharide domain of the immunoadjuvant jujuboside A: Via convergent B(C6F5)3-catalyzed glycosylation of sterically-hindered precursors". supporting information. p. 5838 - 5841. Retrieved 2017/07/11.
• 2、 Kaji, Eisuke,Yamamoto, Daisuke,Shirai, Yuko,Ishige, Koji,Arai, Yoshika,Shirahata, Tatsuya,Makino, Kazuishi,Nishino, Takashi. "Thermodynamically controlled regioselective glycosylation of fully unprotected sugars through Bis(boronate) intermediates". supporting information. p. 3536 - 3539. Retrieved 2014/06/23.