Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano

Base Information

• Chemical Name: Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano
• CAS No.: 303127-85-7
• Molecular Formula: C₃₀H₂₈Cl₃NO₈
• Molecular Weight: 636.913

Synonyms:Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano

Chemical Property of Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano

Chemical Property:

Purity/Quality:

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Technology Process of Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano

There total 8 articles about Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano 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: 71.0%

trichloroacetonitrile (545-06-2) + Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate (303127-84-6) → Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano (303127-85-7)

Guidance literature:

Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate; With ammonium cerium(IV) nitrate; In water; toluene; acetonitrile; at 20 ℃; for 0.333333h;

trichloroacetonitrile; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at 0 ℃; for 0.166667h; Further stages.;

DOI:10.1039/b002835p

Reference yield:

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose (39686-94-7,56632-47-4,65827-58-9,99202-62-7,99202-66-1,103082-79-7,103703-00-0,103703-01-1,118711-49-2,127853-23-0,139563-66-9) → Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano (303127-85-7)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 69 percent / trimethylsilyl triflate; 4 Angstroem molecular sieves / CH₂Cl₂ / 2 h / 0 °C

2.1: 89 percent / methanol / 16 h / 20 °C

3.1: 84 percent / CF₃CO₂H / 0.33 h

4.1: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

5.1: 64 percent / AlCl₃; borane-trimethylamine complex; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 2 h / 0 °C

6.1: 79 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

7.1: 1.56 g / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

8.1: cerium(IV) ammonium nitrite / H₂O; acetonitrile; toluene / 0.33 h / 20 °C

8.2: 71 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; aluminium trichloride; ammonium cerium(IV) nitrate; trimethylsilyl trifluoromethanesulfonate; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; triethylamine; trifluoroacetic acid; In methanol; diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: Etherification / 2.1: Deacetylation / 3.1: Cyclization / 4.1: Acylation / 5.1: Ring cleavage / 6.1: Oxidation / 7.1: Acylation / 8.1: Substitution / 8.2: Addition;

DOI:10.1039/b002835p

Reference yield:

4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside (303127-80-2) → Methyl 2-O-benzoyl-3,4-di-O-benzyl-1-O-trichloroacetimidoyl-α-D-glucopyrano (303127-85-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: 84 percent / CF₃CO₂H / 0.33 h

2.1: 83 percent / pyridine / CH₂Cl₂ / 1.5 h / 0 - 20 °C

3.1: 64 percent / AlCl₃; borane-trimethylamine complex; 4 Angstroem molecular sieves / diethyl ether; CH₂Cl₂ / 2 h / 0 °C

4.1: 79 percent / CrO₃; H₂SO₄ / acetone / 1 h / 20 °C

5.1: 1.56 g / DMAP; Et₃N / CH₂Cl₂ / 2 h / 0 - 20 °C

6.1: cerium(IV) ammonium nitrite / H₂O; acetonitrile; toluene / 0.33 h / 20 °C

6.2: 71 percent / DBU / CH₂Cl₂ / 0.17 h / 0 °C

With pyridine; chromium(VI) oxide; dmap; aluminium trichloride; ammonium cerium(IV) nitrate; trimethylamine-borane; 4 A molecular sieve; sulfuric acid; triethylamine; trifluoroacetic acid; In diethyl ether; dichloromethane; water; acetone; toluene; acetonitrile; 1.1: Cyclization / 2.1: Acylation / 3.1: Ring cleavage / 4.1: Oxidation / 5.1: Acylation / 6.1: Substitution / 6.2: Addition;

DOI:10.1039/b002835p

upstream raw materials:

trichloroacetonitrile

Methyl (4-methoxyphenyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosid)uronate

1,2,4,6-tetra-O-acetyl-3-O-benzyl-β-D-glucopyranose

4-Methoxyphenyl 3-O-benzyl-β-D-glucopyranoside

Downstream raw materials:

Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

Benzyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosyluronate)-(1->3)-4-O-benzyl-6-O-(tert-butyldimethylsilyl)-2-deoxy-2-trichloroacetamido-β-D-galactopyranoside

(2S,3S,4R,5R,6R)-6-((2R,3R,4R,5R,6R)-3-Acetylamino-5-benzyloxy-6-hydroxymethyl-2-methoxy-tetrahydro-pyran-4-yloxy)-3,4-bis-benzyloxy-5-hydroxy-tetrahydro-pyran-2-carboxylic acid

Methyl O-(methyl 2-O-benzoyl-3,4-di-O-benzyl-β-D-glucopyranosylunorate)-(1->3)-2-acetamido-4-O-benzyl-2-deoxy-β-D-galactopyranoside

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