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

Base Information

Chemical Name:allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside
CAS No.:147577-17-1
Molecular Formula:C₃₃H₄₀O₁₃
Molecular Weight:644.673
Hs Code.:

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

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

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

There total 9 articles about allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-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: 62.0%

: 147577-45-5
allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-6-O-(4-methoxybenzyl)-β-D-glucopyranoside

: 147577-17-1
allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:: With ammonium cerium(IV) nitrate; In water; acetonitrile; for 1h; Ambient temperature;
DOI:10.1016/S0008-6215(92)84233-I

Reference yield:

: 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
allyl β-D-glucopyranoside

: 147577-17-1
allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 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

With pyridine; ammonium cerium(IV) nitrate; 3 A molecular sieve; 4 A molecular sieve; silver trifluoromethanesulfonate; sodium cyanoborohydride; toluene-4-sulfonic acid; trifluoroacetic acid; tetramethylurea; In dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/S0008-6215(92)84233-I

Reference yield:

: 136737-65-0
allyl 2,4-di-O-methyl-α-L-fucopyranoside

: 147577-17-1
allyl O-(3-O-acetyl-2,4-di-O-methyl-α-L-fucopyranosyl)-(1->4)-2,3-di-O-benzoyl-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 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

With pyridine; 1,4-diaza-bicyclo[2.2.2]octane; Wilkinson's catalyst; ammonium cerium(IV) nitrate; 4 A molecular sieve; Vilsmeier reagent; silver trifluoromethanesulfonate; tetramethylurea; mercury dichloride; mercury(II) oxide; In dichloromethane; water; acetonitrile;
DOI:10.1016/S0008-6215(92)84233-I