benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Base Information

• Chemical Name: benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate
• CAS No.: 130841-39-3
• Molecular Formula: C₄₆H₄₇NO₈
• Molecular Weight: 741.881
• Mol file: 130841-39-3.mol

Synonyms:benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Chemical Property of benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate

There total 4 articles about benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate 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: 95.0%

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid (125288-69-9) + benzyl bromide (100-39-0) → benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (130841-39-3)

Guidance literature:

With potassium fluoride; In N,N-dimethyl-formamide; Ambient temperature;

DOI:10.1016/S0968-0896(96)00172-1

Reference yield: 64.0%

(2S,4S,5R,6R)-5-Acetylamino-4-benzyloxy-2-(toluene-4-sulfinyl)-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester → benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (130841-39-3)

Guidance literature:

In toluene; Heating;

DOI:10.1016/S0040-4039(02)00555-5

Reference yield:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate (25875-99-4,79026-38-3) → methyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (116096-63-0) + Methyl 5-Acetamido-4,8,9-tri-O-benzyl-3,5-dideoxy-d-glycero-d-galacto-non-2-enonate (131318-26-8) + benzyl 5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonate (130841-39-3) + Methyl 5-(N-acetyl-N-benzylamino)-4,7,8,9-tetra-O-benzyl-3,5-dideoxy-D-glycero-d-galacto-non-2-enonate (131292-56-3)

Guidance literature:

With sodium hydride; Yield given. Multistep reaction. Yields of byproduct given; 1.) DMF, 1 h, RT, 2.) 1 h, RT;

DOI:10.1002/hlca.19900730522

upstream raw materials:

methyl 5-acetamido-2,6-anhydro-3,5-dideoxy-D-glycero-D-galacto-non-2-enonate

benzyl bromide

5-acetamido-4,7,8,9-tetra-O-benzyl-2,3-dehydro-3,5-dideoxy-D-glycero-D-galacto-2-nonulopyranosonic acid

Downstream raw materials:

(2R,3R,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2R,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-hydroxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2R,3S,4R,5S,6R)-5-Acetylamino-4-benzyloxy-2-methylsulfanyl-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester

(2S,3S,4R,5S,6R)-2-Acetoxy-5-acetylamino-4-benzyloxy-3-phenylsulfanyl-6-((1S,2R)-1,2,3-tris-benzyloxy-propyl)-tetrahydro-pyran-2-carboxylic acid benzyl ester