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

Base Information

Chemical Name: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
CAS No.:311779-05-2
Molecular Formula:C₆₆H₇₃NO₁₇
Molecular Weight:1152.3
Hs Code.:

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

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 10 articles about 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 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: 81.0%

: 50605-04-4
methyl 2-acetamido-2-deoxy-4,6-O-isopropylidene-β-D-glucopyranoside

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

: 311779-05-2
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

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -10 ℃;
DOI:10.1080/07328300008544123

Reference yield:

: 100639-25-6,71695-57-3
allyl 2,3-O-isopropylidene-α-L-rhamnopyranoside

: 311779-05-2
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

Guidance literature:: Multi-step reaction with 8 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

8: 81 percent / BF₃*Et₂O / CH₂Cl₂ / -10 °C

With pyridine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; trifluoromethylsulfonic anhydride; boron trifluoride diethyl etherate; 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 / 8: Substitution;
DOI:10.1080/07328300008544123

Reference yield:

: 98-88-4
benzoyl chloride

: 311779-05-2
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

Guidance literature:: Multi-step reaction with 5 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

5: 81 percent / BF₃*Et₂O / CH₂Cl₂ / -10 °C

With pyridine; (1,5-cyclooctadiene)bis(methyldiphenylphosphine) iridium hexafluorophosphate; boron trifluoride diethyl etherate; water; 1,8-diazabicyclo[5.4.0]undec-7-ene; mercury dichloride; mercury(II) oxide; In tetrahydrofuran; dichloromethane; 1,2-dichloro-ethane; acetone; 1: Acylation / 2: Isomerization / 3: Hydrolysis / 4: Addition / 5: Substitution;
DOI:10.1080/07328300008544123