benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose

Base Information

• Chemical Name: benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose
• CAS No.: 26623-26-7
• Molecular Formula: C₁₆H₂₀O₅
• Molecular Weight: 292.332
• Mol file: 26623-26-7.mol

Synonyms:benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose

Chemical Property of benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose

There total 11 articles about benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-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: 77.0%

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (53270-14-7) → benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose (26623-26-7)

Guidance literature:

With ruthenium tetroxide; for 1h;

Reference yield:

α-D-rhamnopyranose (643-17-4) → benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose (26623-26-7)

Guidance literature:

Multi-step reaction with 6 steps

1: 100 percent / pyridine / Ambient temperature

2: 88 percent / HBr in acetic acid / CH₂Cl₂ / 3 h / 0 °C

3: 82 percent / mercuric cianid / CH₂Cl₂ / 16 h / Ambient temperature

4: 95 percent / 1M sodium methoxide / methanol / 1 h / Ambient temperature

5: 90 percent / p-toluenesulfonic acid / 0.75 h / Ambient temperature

6: 1.) potassium periodate, potassium carbonate, RhO₂; 2.) 2-propanol / 1.) 7 h, r.t.; 2.) r.t., 20 min

With rhodium(IV) oxide; potassium metaperiodate; hydrogen bromide; sodium methylate; mercury(II) cyanide; potassium carbonate; toluene-4-sulfonic acid; isopropyl alcohol; In pyridine; methanol; dichloromethane;

DOI:10.1016/0008-6215(83)84006-3

Reference yield:

2,3,4-tri-O-acetyl-α-L-rhamnopyranosyl bromide (5158-64-5,14227-85-1,16741-27-8,24404-52-2,24877-07-4,36807-84-8,39524-38-4,41881-45-2,60978-06-5,69483-13-2,69980-52-5,75247-28-8,75247-29-9,80483-13-2,80483-14-3,89301-86-0,96648-29-2,108942-35-4,108942-38-7,138514-69-9) → benzyl 6-deoxy-2,3-O-isopropylidene-α-L-lyxo-hexopyranosid-4-ulose (26623-26-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 82 percent / mercuric cianid / CH₂Cl₂ / 16 h / Ambient temperature

2: 95 percent / 1M sodium methoxide / methanol / 1 h / Ambient temperature

3: 90 percent / p-toluenesulfonic acid / 0.75 h / Ambient temperature

4: 1.) potassium periodate, potassium carbonate, RhO₂; 2.) 2-propanol / 1.) 7 h, r.t.; 2.) r.t., 20 min

With rhodium(IV) oxide; potassium metaperiodate; sodium methylate; mercury(II) cyanide; potassium carbonate; toluene-4-sulfonic acid; isopropyl alcohol; In methanol; dichloromethane;

DOI:10.1016/0008-6215(83)84006-3

upstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

(2R,3R,4R,5R,6S)-2-benzyloxy-tetrahydro-6-methyl-2H-pyran-3,4,5-triol

L-Rhamnose

benzyl alcohol

Downstream raw materials:

benzyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

benzyl 6-deoxy-2,3-O-isopropylidene-α-L-talopyranoside

(3aR,4R,6S,6aR)-4-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[3,4-d][1,3]dioxole

benzyl 5-deoxy-2,3-O-isopropylidene-β-D-ribofuranoside