methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Base Information

• Chemical Name: methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate
• CAS No.: 147577-18-2
• Molecular Formula: C₃₄H₄₀O₁₄
• Molecular Weight: 672.683
• Mol file: 147577-18-2.mol

Synonyms:

Chemical Property of methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate

There total 11 articles about methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate 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:

allyl β-D-glucopyranoside (2595-07-5,7464-56-4,34384-79-7,41308-76-3,48149-72-0,48149-74-2,85249-43-0,119479-69-5,821794-45-0) → methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (147577-18-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 76.5 percent / p-toluenesulfonic acid / dimethylformamide / a) room temperature, overnight, b) 50 deg C, diminished pressure, 2.5 h

2: 84 percent / pyridine / Ambient temperature

3: 62 percent / sodium cyanoborohydride, 3A molecular sieves, trifluoroacetic acid, / dimethylformamide / 7 h / 0 °C

4: 43 percent / silver trifluoromethanesulfonate, tetramethylurea, 4A molecular sieves / CH₂Cl₂ / -78 deg C to room temperature, overnight

5: 62 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

6: chromium trioxide, 3.5 M H₂SO₄ / acetone / 1 h / Ambient temperature

7: CH₂Cl₂

With pyridine; chromium(VI) oxide; ammonium cerium(IV) nitrate; 3 A molecular sieve; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; tetramethylurea; In dichloromethane; water; N,N-dimethyl-formamide; acetone; acetonitrile;

DOI:10.1016/S0008-6215(92)84233-I

Reference yield:

allyl 2,4-di-O-methyl-α-L-fucopyranoside (136737-65-0) → methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (147577-18-2)

Guidance literature:

Multi-step reaction with 7 steps

1: 92 percent / pyridine

2: 1) tris(triphenylphosphine)rhodium(I) chloride, 1,4-diazabicyclo<2.2.2>octane, 2) mercuric oxide, mercuric chloride / 1) EtOH, toluene, water, reflux, 17 h, 2) acetone, water, room temperature, 2 h

3: N,N-dimethyl(chloromethylene)ammonium chloride

4: 43 percent / silver trifluoromethanesulfonate, tetramethylurea, 4A molecular sieves / CH₂Cl₂ / -78 deg C to room temperature, overnight

5: 62 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

6: chromium trioxide, 3.5 M H₂SO₄ / acetone / 1 h / Ambient temperature

7: CH₂Cl₂

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; chromium(VI) oxide; Wilkinson's catalyst; ammonium cerium(IV) nitrate; 4 A molecular sieve; sulfuric acid; Vilsmeier reagent; silver trifluoromethanesulfonate; tetramethylurea; mercury dichloride; mercury(II) oxide; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0008-6215(92)84233-I

Reference yield:

Acetic acid (3S,4R,5R,6S)-2-chloro-3,5-dimethoxy-6-methyl-tetrahydro-pyran-4-yl ester → methyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-(allyl 2,3-di-O-benzoyl-β-D-glucopyranosid)uronate (147577-18-2)

Guidance literature:

Multi-step reaction with 4 steps

1: 43 percent / silver trifluoromethanesulfonate, tetramethylurea, 4A molecular sieves / CH₂Cl₂ / -78 deg C to room temperature, overnight

2: 62 percent / ceric ammonium nitrate / acetonitrile; H₂O / 1 h / Ambient temperature

3: chromium trioxide, 3.5 M H₂SO₄ / acetone / 1 h / Ambient temperature

4: CH₂Cl₂

With chromium(VI) oxide; ammonium cerium(IV) nitrate; 4 A molecular sieve; sulfuric acid; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; water; acetone; acetonitrile;

DOI:10.1016/S0008-6215(92)84233-I

upstream raw materials:

diazomethane

allyl β-D-glucopyranoside

allyl 2,4-di-O-methyl-α-L-fucopyranoside

allyl 3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranoside