(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate

Base Information

• Chemical Name: (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate
• CAS No.: 311779-18-7
• Molecular Formula: C₅₆H₅₄Cl₃NO₁₂
• Molecular Weight: 1039.4

Synonyms:(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate

Chemical Property of (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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Technology Process of (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate

There total 8 articles about (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate 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: 83.0%

trichloroacetonitrile (545-06-2) + 2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranose (311779-16-5) → (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (311779-18-7)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In 1,2-dichloro-ethane; at 0 ℃; for 0.5h;

DOI:10.1080/07328300008544123

Reference yield:

allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside (100639-25-6,71695-57-3) → (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (311779-18-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 96 percent / pyridine / CH₂Cl₂ / 2 h / 20 °C

2: 55 percent / Tf₂O / diethyl ether / 17 h / -25 - 0 °C

3: 95 percent / AcOH; H₂O / 4 h / 60 °C

4: 90 percent / pyridine / 72 h / 20 °C

5: 1,5-cyclooctadiene-(Ph₂PMe)2-iridium hexafluorophosphate / tetrahydrofuran / 2 h

6: mercuric chloride; mercuric oxide; H₂O / acetone / 1 h / 20 °C

7: 83 percent / DBU / 1,2-dichloro-ethane / 0.5 h / 0 °C

With pyridine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trifluoromethylsulfonic anhydride; water; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; diethyl ether; dichloromethane; 1,2-dichloro-ethane; acetone; 1: Substitution / 2: Substitution / 3: Hydrolysis / 4: Acylation / 5: Isomerization / 6: Hydrolysis / 7: Addition;

DOI:10.1080/07328300008544123

Reference yield:

benzoyl chloride (98-88-4) → (2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranosyl trichloroacetimidate (311779-18-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 90 percent / pyridine / 72 h / 20 °C

2: 1,5-cyclooctadiene-(Ph₂PMe)2-iridium hexafluorophosphate / tetrahydrofuran / 2 h

3: mercuric chloride; mercuric oxide; H₂O / acetone / 1 h / 20 °C

4: 83 percent / DBU / 1,2-dichloro-ethane / 0.5 h / 0 °C

With pyridine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; 1,2-dichloro-ethane; acetone; 1: Acylation / 2: Isomerization / 3: Hydrolysis / 4: Addition;

DOI:10.1080/07328300008544123

upstream raw materials:

trichloroacetonitrile

2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl-(1->4)-2,3-di-O-benzoyl-α-L-rhamnopyranose

allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

benzoyl chloride

Downstream raw materials:

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-(2,3-di-O-benzoyl-α-L-rhamnopyranosyl)-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranosyl-(1->3)-2-acetamido-2-deoxy-β-D-glucopyranoside

methyl (2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-(1->4)-α-L-rhamnopyranosyl-(1->3)-2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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