Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Base Information

• Chemical Name: Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside
• CAS No.: 148168-52-9
• Molecular Formula: C₄₈H₅₄O₁₀
• Molecular Weight: 790.951
• Mol file: 148168-52-9.mol

Synonyms:

Chemical Property of Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside

There total 6 articles about Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside 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,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol (35303-86-7) → Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (148168-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 3 h / 0 °C

2: 80 percent / Na, MeOH / 2 h

3: 89 percent / NaH / paraffin; tetrahydrofuran

4: 1.) 1,4-diazabicyclo<2.2.2>octane, 2.) mercuric chloride, mercuric oxide / 1.) tris(triphenylphosphine)rhodium(I)chloride / 1.) EtOH, benzene, H₂O, 100 deg C, 20 h, 2.) acetone, water, r.t., 1 h

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium; sodium hydride; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; paraffin;

DOI:10.1016/0008-6215(93)84227-W

Reference yield:

benzyl bromide (100-39-0) → Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (148168-52-9)

Guidance literature:

Multi-step reaction with 2 steps

1: 89 percent / NaH / paraffin; tetrahydrofuran

2: 1.) 1,4-diazabicyclo<2.2.2>octane, 2.) mercuric chloride, mercuric oxide / 1.) tris(triphenylphosphine)rhodium(I)chloride / 1.) EtOH, benzene, H₂O, 100 deg C, 20 h, 2.) acetone, water, r.t., 1 h

With 1,4-diaza-bicyclo[2.2.2]octane; sodium hydride; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; paraffin;

DOI:10.1016/0008-6215(93)84227-W

Reference yield:

1,2-Di-O-acetyl-3-O-allyl-4-O-benzyl-α,β-L-rhamnopyranose (163660-77-3) → Methyl 2,4,6-tri-O-benzyl-3-O-(2,4-di-O-benzyl-α-L-rhamnopyranosyl)-α-D-glucopyranoside (148168-52-9)

Guidance literature:

Multi-step reaction with 4 steps

1: 44 percent / BF₃*Et₂O, 4A molecular sieves / CH₂Cl₂ / 3 h / 0 °C

2: 80 percent / Na, MeOH / 2 h

3: 89 percent / NaH / paraffin; tetrahydrofuran

4: 1.) 1,4-diazabicyclo<2.2.2>octane, 2.) mercuric chloride, mercuric oxide / 1.) tris(triphenylphosphine)rhodium(I)chloride / 1.) EtOH, benzene, H₂O, 100 deg C, 20 h, 2.) acetone, water, r.t., 1 h

With 1,4-diaza-bicyclo[2.2.2]octane; methanol; 4 A molecular sieve; boron trifluoride diethyl etherate; sodium; sodium hydride; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In tetrahydrofuran; dichloromethane; paraffin;

DOI:10.1016/0008-6215(93)84227-W

upstream raw materials:

C₅₁H₅₈O₁₀

(2R,3S,4S,5R,6S)-3,5-Bis-benzyloxy-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran-4-ol

benzyl bromide

1,2-Di-O-acetyl-3-O-allyl-4-O-benzyl-α,β-L-rhamnopyranose