methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside

Base Information

• Chemical Name: methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside
• CAS No.: 72159-38-7
• Molecular Formula: C₁₇H₂₁NO₈
• Molecular Weight: 367.356
• Mol file: 72159-38-7.mol

Synonyms:methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside

Chemical Property of methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside

There total 5 articles about methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside 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: 80.0%

methyl 6-deoxy-2,3-O-isopropylidene-alpha-L-talo-furanoside (28538-26-3) + 4-nitro-benzoic acid (62-23-7) → methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside (72159-38-7)

Guidance literature:

With triphenylphosphine; diethylazodicarboxylate; In 1,4-dioxane; for 16h; Ambient temperature;

DOI:10.1080/15257779508012498

Reference yield: 52.0%

4-nitro-benzoyl chloride (122-04-3) + methyl 2,3-O-isopropylidene-6-deoxy-β-D-allofuranoside (53270-44-3) → methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside (72159-38-7)

Guidance literature:

In pyridine; for 12h; Ambient temperature;

DOI:10.1016/S0008-6215(00)80814-9

Reference yield:

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde (33985-40-9) → methyl 6-deoxy-2,3-O-isopropylidene-5-O-(p-nitrobenzoyl)-beta-D-allofuranoside (72159-38-7)

Guidance literature:

Multi-step reaction with 2 steps

1: various solvent(s); diethyl ether / 4 h / Ambient temperature

2: 52 percent / pyridine / 12 h / Ambient temperature

In pyridine; diethyl ether;

DOI:10.1016/S0008-6215(00)80814-9

upstream raw materials:

methyl magnesium iodide

(3aR,4S,6R,6aR)-tetrahydro-6-methoxy-2,2-dimethylfuro-[3,4-d][1,3]dioxole-4-carbaldehyde

4-nitro-benzoyl chloride

methyl 2,3-O-isopropylidene-6-deoxy-β-D-allofuranoside

Downstream raw materials:

methyl 6-deoxy-5-o-(p-nitrobenzoyl)-beta-D-allofuranoside

6-deoxy-2,3,5-tri-O-(p-nitrobenzoyl)-beta-D-allofuranosyl bromide

methyl 6-deoxy-2,3,5-tri-O-(p-nitrobenzoyl)-beta-D-allofuranoside