[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate

Base Information

• Chemical Name: [(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate
• CAS No.: 6920-00-9
• Molecular Formula: C28H38O19
• Molecular Weight: 678.598
• DSSTox Substance ID: DTXSID30466014
• Nikkaji Number: J1.310.199J
• Wikidata: Q82292375
• Mol file: 6920-00-9.mol

Synonyms:6920-00-9;[(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate;?-D-Maltose Octaacetate;DTXSID30466014;1,2,3,6-Tetra-O-acetyl-4-O-(2,3,4,6-tetra-O-acetyl-|A-D-glucopyranosyl)-|A-D-glucopyranose

Chemical Property of [(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate

Chemical Property:

• PSA: 238.09000
• LogP: -0.82920
• Storage Temp.: ?20°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• 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:

97% ^*data from raw suppliers

a-D-Maltose 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)OC(=O)C)OC(=O)C)OC(=O)C)OC2C(C(C(C(O2)COC(=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(=O)C)OC(=O)C)OC(=O)C)O[C@@H]2[C@@H]([C@H]([C@@H]([C@H](O2)COC(=O)C)OC(=O)C)OC(=O)C)OC(=O)C
• Uses: Protected Maltose.

Technology Process of [(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate

There total 1 articles about [(2R,3R,4S,5R,6R)-4,5,6-triacetyloxy-3-[(2R,3R,4S,5R,6R)-3,4,5-triacetyloxy-6-(acetyloxymethyl)oxan-2-yl]oxyoxan-2-yl]methyl acetate 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:

acetic anhydride (108-24-7) + syringic aldehyde (134-96-3) + 2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,42385-75-1,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0) → 4-acetoxy-3,5-dimethoxybenzaldehyde (53669-33-3) + 1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) + 3,5-Dimethoxy-4-4)-2,3,6-tri-O-acetyl-β-D-glucopyranosyloxy>benzaldehyde (141243-30-3)

Guidance literature:

With pyridine; sodium hydroxide; Yield given. Multistep reaction; 1) acetone, r.t., 2) 90 deg C, 50 min.;

DOI:10.1016/S0008-6215(00)90495-6

Reference yield: 95.0%

thiophenol (108-98-5) + 1',2',3',6',2,3,4,6-octa-O-acetyl-β-D-lactose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-60-8,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4) → phenyl 2,3,6-tri-O-acetyl-4-O-(2',3',4',6'-tetra-O-acetyl-β-D-galactopyranosyl)-1-thio-β-D-glucopyranoside (5346-81-6,28022-14-2,28022-13-1)

Guidance literature:

With molybdenium(VI) dioxodichloride; In dichloromethane; at 20 ℃; for 14h;

DOI:10.1021/ol062375g

Reference yield: 92.0%

1,2,3,6,2',3',4',6'-octa-O-acetylmaltose (3616-19-1,5328-50-7,5346-90-7,6291-42-5,6920-00-9,20764-63-0,20880-65-3,22352-19-8,23973-20-8,32447-69-1,34213-32-6,52554-32-2,53956-64-2,56907-29-0,56994-12-8,56994-13-9,57128-38-8,67650-36-6,68036-17-9,68036-19-1,78215-50-6,78215-51-7,79549-48-7,80446-82-8,85249-04-3,93221-83-1,93779-27-2,111407-83-1,111407-84-2,111407-85-3,120328-65-6,123809-59-6,132341-46-9,132341-47-0,132341-49-2,145307-94-4,20880-60-8) → α-hepta-O-acetylmaltosyl bromide (4753-07-5,5160-10-1,14206-57-6,14227-66-8,14257-35-3,67650-37-7,68682-05-3,69308-57-2,69349-74-2,70223-96-0,70223-97-1,71276-38-5,85248-99-3,118493-15-5,120575-76-0,42385-75-1)

Guidance literature:

With hydrogen bromide; In acetic acid;

DOI:10.1016/0040-4039(96)01021-0

upstream raw materials:

acetic anhydride

syringic aldehyde

2,3,6,2',3',4',6'-hepta-O-acetyl-α-D-maltosyl bromide

Downstream raw materials:

4-nitrophenyl-2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tetra-O-acetyl-β-D-glucopyranoside

phenyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl-(1→4)-2,3,6-tri-O-acetyl-α-D-glucopyranoside

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

O²,O³,O⁶-Triacetyl-O⁴-(tetra-O-acetyl-β-D-galactopyranosyl)-D-glucose

Refernces