Methyl 3,6-Di-O-(α-D-Mannopyranosyl)-2-O-(2-propenyl)-α-D-Mannopyranoside Octaacetate

Base Information

• Chemical Name: Methyl 3,6-Di-O-(α-D-Mannopyranosyl)-2-O-(2-propenyl)-α-D-Mannopyranoside Octaacetate
• CAS No.: 82185-94-2
• Molecular Formula: C₃₈H₅₄O₂₄
• Molecular Weight: 894.832
• Mol file: 82185-94-2.mol

Synonyms:

Chemical Property of Methyl 3,6-Di-O-(α-D-Mannopyranosyl)-2-O-(2-propenyl)-α-D-Mannopyranoside Octaacetate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Methyl3,6-Di-O-(α-D-mannopyranosyl)-2-O-(2-propenyl)-α-D-mannopyranosideOctaacetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Intermediate in the preparation of Methyl 3,6-Di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside (M302500).

Technology Process of Methyl 3,6-Di-O-(α-D-Mannopyranosyl)-2-O-(2-propenyl)-α-D-Mannopyranoside Octaacetate

There total 6 articles about Methyl 3,6-Di-O-(α-D-Mannopyranosyl)-2-O-(2-propenyl)-α-D-Mannopyranoside 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: 67.0%

methyl 2-O-allyl-3-O-(tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (81555-75-1) + acetobromomannose (13242-53-0) → methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (82185-94-2)

Guidance literature:

With 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In acetonitrile; for 1h; Ambient temperature;

DOI:10.1016/S0008-6215(82)80004-9

Reference yield:

methyl-4,6-O-phenylmethylene-α-D-mannopyranoside (3162-96-7,4148-58-7,4153-17-7,4288-93-1,5328-47-2,6988-39-2,13566-32-0,14155-23-8,27994-50-9,37093-57-5,37093-59-7,57701-27-6,59168-66-0,64552-06-3,65391-13-1,65391-14-2,65530-26-9,66512-65-0,71117-36-7,71117-37-8,71117-41-4,72904-85-9,74560-56-8,79549-74-9,86783-81-5,96093-51-5,98633-13-7,110415-35-5,110415-36-6,110850-29-8,124020-29-7,126924-12-7,129263-21-4,131433-03-9,145920-49-6,146863-04-9) → methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (82185-94-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 76 percent / 50 percent sodium hydroxide / tetra-butylammonium hydrogen sulfate / CH₂Cl₂; H₂O / 20 h / Heating

2: 90 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature

3: 78 percent / 60 percent acetic acid / H₂O / 0.5 h / 80 °C / Heating

4: 67 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature

With sodium hydroxide; 4 A molecular sieve; mercury(II) cyanide; acetic acid; mercury dibromide; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; water; acetonitrile;

DOI:10.1016/S0008-6215(82)80004-9

Reference yield:

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose (3254-16-8,4435-05-6,19189-54-9,29748-21-8,50801-29-1,64727-26-0,64727-27-1,65338-02-5,67672-68-8,78418-55-0,80877-03-8,103002-27-3,103002-29-5,132562-62-0) → methyl 2-O-allyl-3,6-di-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside (82185-94-2)

Guidance literature:

Multi-step reaction with 2 steps

1: bromotrimethylsilane / CH₂Cl₂ / 2 h / Heating

2: 67 percent / mercuric bromide, mercuric cyanide, 4A molecular sieves / acetonitrile / 1 h / Ambient temperature

With trimethylsilyl bromide; 4 A molecular sieve; mercury(II) cyanide; mercury dibromide; In dichloromethane; acetonitrile;

DOI:10.1016/S0008-6215(82)80004-9

upstream raw materials:

methyl 2-O-allyl-3-O-(tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

acetobromomannose

3,4,6-tri-O-acetyl-1,2-O-(1-methoxyethylidene)-β-D-mannopyranose

methyl 2-O-allyl-4,6-O-benzylidene-3-O-(2,3,4,6-tetra-O-acetyl-α-D-mannopyranosyl)-α-D-mannopyranoside

Downstream raw materials:

methyl 3,6-di-O-(α-D-mannopyranosyl)-α-D-mannopyranoside