8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 134136-29-1
• Molecular Formula: C₈₀H₉₁NO₁₈
• Molecular Weight: 1354.6

Synonyms:

Chemical Property of 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside

There total 13 articles about 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside 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%

2-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranosyl chloride (72599-87-2) + 8-(methoxycarbonyl)octyl 4-O-benzyl-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside (134136-27-9) → 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside (134136-29-1)

Guidance literature:

With 4 A molecular sieve; silver trifluoromethanesulfonate; tetramethylurea; In dichloromethane; for 34h; Ambient temperature;

DOI:10.1016/0008-6215(91)80123-5

Reference yield:

benzyl bromide (100-39-0) → 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside (134136-29-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaH / 1) THF, 15 min, 2) THF, 36 h, r. t.

2: Rh(PPh₃)3Cl / ethanol; H₂O / 18 h / Heating

3: HgO(yellow), HgCl₂ / acetone; H₂O / 18 h

4: 97 percent / oxalyl chloride, DMF / CH₂Cl₂ / 2 h / 0 °C

5: 56.9 percent / CF₃SO₃Ag, collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / 72 h / Ambient temperature

6: 58 percent / 0.1 M NaOMe / 36 h / Ambient temperature

7: 62 percent / CF₃SO₃Ag, 1,1,3,3-tetramethylurea, 4 Angstroem molecular sieves / CH₂Cl₂ / 34 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; oxalyl dichloride; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; N,N-dimethyl-formamide; tetramethylurea; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In ethanol; dichloromethane; water; acetone;

DOI:10.1016/0008-6215(91)80123-5

Reference yield:

allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside (114853-29-1) → 8-(methoxycarbonyl)octyl 2-O-(2-O-acetyl-3,4-di-O-benzyl-α-L-rhamnopyranosyl)-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-4-O-benzyl-α-L-rhamnopyranoside (134136-29-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 1) NaH / 1) THF, 15 min, 2) THF, 36 h, r. t.

2: Rh(PPh₃)3Cl / ethanol; H₂O / 18 h / Heating

3: HgO(yellow), HgCl₂ / acetone; H₂O / 18 h

4: 97 percent / oxalyl chloride, DMF / CH₂Cl₂ / 2 h / 0 °C

5: 56.9 percent / CF₃SO₃Ag, collidine, 4 Angstroem molecular sieves / CH₂Cl₂ / 72 h / Ambient temperature

6: 58 percent / 0.1 M NaOMe / 36 h / Ambient temperature

7: 62 percent / CF₃SO₃Ag, 1,1,3,3-tetramethylurea, 4 Angstroem molecular sieves / CH₂Cl₂ / 34 h / Ambient temperature

With 2,3,5-trimethyl-pyridine; oxalyl dichloride; 4 A molecular sieve; sodium methylate; silver trifluoromethanesulfonate; sodium hydride; N,N-dimethyl-formamide; tetramethylurea; mercury dichloride; mercury(II) oxide; Wilkinson's catalyst; In ethanol; dichloromethane; water; acetone;

DOI:10.1016/0008-6215(91)80123-5

upstream raw materials:

2-O-acetyl-3,4-di-O-benzyl-6-deoxy-α-L-mannopyranosyl chloride

8-(methoxycarbonyl)octyl 4-O-benzyl-3-O-(3,4,6-tri-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl)-α-L-rhamnopyranoside

benzyl bromide

allyl 2-deoxy-2-phthalimido-β-D-glucopyranoside

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