methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

Base Information

• Chemical Name: methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose
• CAS No.: 135700-48-0
• Molecular Formula: C₁₇H₂₀O₅
• Molecular Weight: 304.343
• Mol file: 135700-48-0.mol

Synonyms:methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

Chemical Property of methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose

There total 12 articles about methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose 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:

(2R,4aR,6S,8aS)-8-Allyl-6-methoxy-2-phenyl-tetrahydro-pyrano[3,2-d][1,3]dioxin-7-one → methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose (135700-48-0)

Guidance literature:

With silica gel; In pyridine; at 80 - 90 ℃;

DOI:10.1021/jo982199s

Reference yield:

Methyl 2-O-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-2-enopyranoside (138638-80-9) → methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose (135700-48-0)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / 3 h / 80 - 90 °C

2: 0.24 g / silica gel / pyridine / 80 - 90 °C

With pyridine; silica gel; In pyridine; 1: Rearrangement / 2: Isomerization;

DOI:10.1021/jo982199s

Reference yield:

methyl 4,6-O-(phenylmethylene)-3-deoxy-3-(4-morpholinyl)-α-D-altro-pyranoside (256455-94-4) → methyl 4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-arabino-hexopyranoside-2-ulose (135700-48-0)

Guidance literature:

Multi-step reaction with 5 steps

1.1: NaH / dimethylformamide / 0.5 h / 20 °C

1.2: 85 percent / dimethylformamide / 4.5 h / 20 °C

2.1: mCPBA / CH₂Cl₂ / 0.5 h / 20 °C

3.1: pyridine / 80 - 100 °C

4.1: pyridine / 3 h / 80 - 90 °C

5.1: 0.24 g / silica gel / pyridine / 80 - 90 °C

With pyridine; silica gel; sodium hydride; 3-chloro-benzenecarboperoxoic acid; In pyridine; dichloromethane; N,N-dimethyl-formamide; 1.1: deprotonation / 1.2: Alkylation / 2.1: Oxidation / 3.1: Elimination / 4.1: Rearrangement / 5.1: Isomerization;

DOI:10.1021/jo982199s

upstream raw materials:

Methyl 3-C-allyl-4,6-O-benzylidene-α-D-ribo-hexopyranosid-2-ulose

methyl 4,6-O-benzylidene-3-deoxy-3-(prop-2-enyl)-α-D-altropyranoside

Methyl 2-O-allyl-4,6-O-benzylidene-3-deoxy-α-D-erythro-hex-2-enopyranoside

methyl 4,6-O-(phenylmethylene)-3-deoxy-3-(4-morpholinyl)-α-D-altro-pyranoside

Downstream raw materials:

methyl α-D-4,6-O-((R)-benzylidene)-3-deoxy-3-(2-oxopropyl)-glucopyranosid-2-ulose

methyl (R)-4,6-O-benzylidene-3-deoxy-3-C-propenyl-α-D-glucopyranoside

methyl 3-C-allyl-2-benzylamino-(R)-4,6-O-benzylidene-2,3-dideoxy-α-D-glucopyranoside

4-benzoyloxy-5-bromomethyl-2,3-C-(2-propen-2'-one)-3-deoxy-3-C-methyl-α-D-arabino-hexopyranosid-2-ulose