Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside

Base Information

• Chemical Name: Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside
• CAS No.: 161147-46-2
• Molecular Formula: C₃₇H₃₅NO₉
• Molecular Weight: 637.686
• Mol file: 161147-46-2.mol

Synonyms:Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside

Chemical Property of Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside

There total 3 articles about Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside 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: 92.0%

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside (103597-22-4) + 4-nitro-benzoic acid (62-23-7) → Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside (161147-46-2)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; for 15h; Ambient temperature;

DOI:10.1021/jo00108a030

Reference yield:

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside (83051-88-1) → Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside (161147-46-2)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi, MgBr₂ / 1.) hexane, Et₂O, -5 deg C, 30 min, 2.) -30 deg C to r.t.

2: 96 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

3: 92 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / Ambient temperature

With n-butyllithium; tetrabutyl ammonium fluoride; triphenylphosphine; magnesium bromide; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00108a030

Reference yield:

(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol (161147-32-6) → Methyl 2,3,4-tri-O-benzyl-7,8-dideoxy-6-O-(p-nitrobenzoyl)-D-glycero-α-D-gluco-hept-7-ynopyranoside (161147-46-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 96 percent / Bu₄NF / tetrahydrofuran / 0.25 h / Ambient temperature

2: 92 percent / Ph₃P, diethyl azodicarboxylate / tetrahydrofuran / 15 h / Ambient temperature

With tetrabutyl ammonium fluoride; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran;

DOI:10.1021/jo00108a030

upstream raw materials:

methyl-2,3,4-tri-O-benzyl-7,7,8,8-tetradehydro-7,8-dideoxy-β-L-glycero-D-gluco-octopyranoside

4-nitro-benzoic acid

methyl 6-aldehydo-2,3,4-tri-O-benzyl-α-D-glucopyranoside

(S)-3-Trimethylsilanyl-1-((2R,3S,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-prop-2-yn-1-ol

Downstream raw materials:

Methyl 6-azido-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

Methyl 6-(N-acetylamino)-2,3,4-tri-O-benzyl-6-deoxy-L-glycero-α-D-gluco-heptopyranosiduronic acid benzyl ester

(R)-Amino-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid benzyl ester

(R)-Azido-((2R,3R,4S,5R,6S)-3,4,5-tris-benzyloxy-6-methoxy-tetrahydro-pyran-2-yl)-acetic acid