3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

Base Information

• Chemical Name: 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose
• CAS No.: 117136-22-8
• Molecular Formula: C₂₇H₂₇NO₆
• Molecular Weight: 461.514
• Mol file: 117136-22-8.mol

Synonyms:3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

Chemical Property of 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose

There total 6 articles about 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose 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:

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide (572-09-8,3068-32-4,4026-32-8,6919-96-6,13242-53-0,14227-54-4,14795-18-7,19186-59-5,19285-38-2,21698-13-5,29907-26-4,53369-42-9,60619-58-1,61303-35-3,67337-79-5,69127-37-3,70749-15-4,72002-90-5,75247-30-2,75880-74-9,78418-57-2,102339-89-9,102339-90-2,103530-40-1,114028-03-4,114718-45-5,138514-70-2,138514-71-3) → 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose (117136-22-8)

Guidance literature:

Multi-step reaction with 4 steps

1: acetic acid; zinc / water / -20 - 0 °C / Inert atmosphere

2: methanol; sodium methylate / 20 °C / Inert atmosphere

3: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 60 °C / Inert atmosphere

4: nitric acid; acetic anhydride / -33 - 25 °C / Inert atmosphere

With methanol; nitric acid; sodium methylate; acetic anhydride; sodium hydride; acetic acid; zinc; In tetrahydrofuran; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol202959y

Reference yield:

D-glucose pentaacetate (83-87-4,604-68-2,604-69-3,2152-77-4,4026-35-1,4163-59-1,4163-60-4,4163-61-5,4163-65-9,4257-94-7,4257-96-9,16299-15-3,19186-39-1,19189-55-0,25878-60-8,25941-03-1,32445-48-0,32445-49-1,32445-53-7,32445-54-8,34685-58-0,34685-59-1,43168-42-9,43168-44-1,43169-22-8,43169-25-1,66966-07-2,70749-17-6,80184-01-6,93221-01-3,93221-02-4,99630-88-3,109215-53-4,115792-70-6,115792-73-9,139894-92-1,139973-25-4,144071-49-8,147648-81-5) → 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose (117136-22-8)

Guidance literature:

Multi-step reaction with 5 steps

1: hydrogen bromide; acetic acid / 12 h / 20 °C / Inert atmosphere

2: acetic acid; zinc / water / -20 - 0 °C / Inert atmosphere

3: methanol; sodium methylate / 20 °C / Inert atmosphere

4: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 60 °C / Inert atmosphere

5: nitric acid; acetic anhydride / -33 - 25 °C / Inert atmosphere

With methanol; hydrogen bromide; nitric acid; sodium methylate; acetic anhydride; sodium hydride; acetic acid; zinc; In tetrahydrofuran; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol202959y

Reference yield:

D-glucal (13265-84-4) → 3,4,6-tri-O-benzyl-1,2-dideoxy-2-nitro-D-arabino-hex-1-enopyranose (117136-22-8)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide; mineral oil / 4 h / 0 - 60 °C / Inert atmosphere

2: nitric acid; acetic anhydride / -33 - 25 °C / Inert atmosphere

With nitric acid; acetic anhydride; sodium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/ol202959y

upstream raw materials:

benzyl bromide

3,4,6-tri-O-benzyl-D-glucal

acetonitrile

2,3,4,6-tetra-O-acetyl-D-glucopyranosyl bromide

Downstream raw materials:

1,5-anhydro-3,4,6-tri-O-benzyl-2-deoxy-1β-(2'-dithianyl)-2-nitro-D-glucitol

dimethyl (3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)malonate

tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-β-D-glucopyranosyl)-D-lactate

tert-butyl O-(3,4,6-tri-O-benzyl-2-deoxy-2-nitro-α-D-glucopyranosyl)-D-lactate