(2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside

Base Information

• Chemical Name: (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside
• CAS No.: 219808-94-3
• Molecular Formula: C₂₁H₂₆O₅
• Molecular Weight: 362.403
• Mol file: 219808-94-3.mol

Synonyms:(2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside

Chemical Property of (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside

There total 7 articles about (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside 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: 82.0%

(2H3)methyl 3,4-di-O-benzyl-β-L-(2-2H)rhamnopyranoside (219808-93-2) → (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside (219808-94-3)

Guidance literature:

With acetyl chloride; In d⁽⁴⁾-methanol; for 1h; Heating;

DOI:10.1016/S0008-6215(98)00254-7

Reference yield:

Allyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside (89821-77-2) → (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside (219808-94-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 70 percent / ethyldiisopropylamine, tris(triphenylphosphine)rhodium(I) chloride / ethanol / 3 h / Heating

2: 91 percent / NaH / tetrahydrofuran / Ambient temperature

3: 92 percent / CF₃COOH / CHCl₃ / 2 h / Ambient temperature

4: 92 percent / dibutyltin oxide / 0.5 h / 90 °C

5: dimethyl sulfoxide, oxalyl chloride, Et₃N / 0.5 h / -60 °C / up to 0 deg C

6: NaBD₄ / tetradeuteriomethanol / 0.25 h

7: 82 percent / acetyl chloride / tetradeuteriomethanol / 1 h / Heating

With Wilkinson's catalyst; sodium borodeuteride; oxalyl dichloride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; ethanol; chloroform; d⁽⁴⁾-methanol;

DOI:10.1016/S0008-6215(98)00254-7

Reference yield:

4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranose (219808-89-6) → (2H3)methyl 3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside (219808-94-3)

Guidance literature:

Multi-step reaction with 6 steps

1: 91 percent / NaH / tetrahydrofuran / Ambient temperature

2: 92 percent / CF₃COOH / CHCl₃ / 2 h / Ambient temperature

3: 92 percent / dibutyltin oxide / 0.5 h / 90 °C

4: dimethyl sulfoxide, oxalyl chloride, Et₃N / 0.5 h / -60 °C / up to 0 deg C

5: NaBD₄ / tetradeuteriomethanol / 0.25 h

6: 82 percent / acetyl chloride / tetradeuteriomethanol / 1 h / Heating

With sodium borodeuteride; oxalyl dichloride; sodium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; triethylamine; acetyl chloride; trifluoroacetic acid; In tetrahydrofuran; chloroform; d⁽⁴⁾-methanol;

DOI:10.1016/S0008-6215(98)00254-7

upstream raw materials:

(2H3)methyl 3,4-di-O-benzyl-β-L-(2-2H)rhamnopyranoside

Allyl 4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranoside

4-O-benzyl-2,3-O-isopropylidene-α-L-rhamnopyranose

(2H3)methyl 4-O-benzyl-β-L-rhamnopyranoside

Downstream raw materials:

(2H3)methyl (2,3,4-tri-O-benzoyl-α-L-rhamnopyranosyl)-(1-> 2)-3,4-di-O-benzyl-α-L-(2-2H)rhamnopyranoside