1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-D-mannopyrannose

Base Information

• Chemical Name: 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-D-mannopyrannose
• CAS No.: 72691-29-3
• Molecular Formula: C₂₈H₃₈O₁₉
• Molecular Weight: 678.598
• Mol file: 72691-29-3.mol

Synonyms:a-D-Mannopyranose,6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-, tetraacetate (9CI)

Chemical Property of 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-D-mannopyrannose

Chemical Property:

• PSA: 238.09000
• LogP: -0.83080

Purity/Quality:

95% ^*data from raw suppliers

1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-D-mannopyrannose ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-D-mannopyrannose

There total 17 articles about 1,2,3,4-Tetra-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-a-D-mannopyranosyl)-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: 87.0%

2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl trichloroimidate (121238-27-5) + acetyl 2,3,4-tri-O-acetyl-α-D-mannopyranoside (51897-82-6) → 2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl-(1→6)-1,2,3,4-tetra-O-acetyl-α-D-mannopyranose (72691-29-3)

Guidance literature:

With boron trifluoride diethyl etherate; Bacillus pumilus xylan esterase immobilized on glyoxyl-agarose; In dichloromethane; at 0 - 20 ℃; for 2.5h; Molecular sieve; Inert atmosphere;

DOI:10.3390/molecules25235764

Reference yield: 72.0%

acetic anhydride (108-24-7) + methyl 2,3,4-tri-O-acetyl-6-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (76951-67-2) → 2',3',4',6'-tetra-O-acetyl-α-D-mannopyranosyl-(1→6)-1,2,3,4-tetra-O-acetyl-α-D-mannopyranose (72691-29-3)

Guidance literature:

With sulfuric acid; 1) 0 deg C; 2) rt;

DOI:10.1080/07328309808002903

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:

(+)-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

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

(+)-menthyl 2,3,4-tri-O-acetyl-6-O-[2,3-di-O-acetyl-4,6-bis-O-(4-bromobenzoyl)-β-D-glucopyranosyl]-β-D-glucopyranoside