methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate

Base Information

• Chemical Name: methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate
• CAS No.: 406460-75-1
• Molecular Formula: C₄₅H₄₆Cl₃NO₁₃
• Molecular Weight: 915.218
• Mol file: 406460-75-1.mol

Synonyms:methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate

Chemical Property of methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate

There total 11 articles about methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate 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: 69.0%

trichloroacetonitrile (545-06-2) + methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate (406460-74-0) → methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate (406460-75-1)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; at -20 - 20 ℃;

DOI:10.1081/CAR-100108276

Reference yield:

methyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside (406460-49-9) → methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate (406460-75-1)

Guidance literature:

Multi-step reaction with 7 steps

1: 90 percent / pyridine / -20 - 20 °C

2: 64 percent / trifluoromethanesulfonic acid / CH₂Cl₂; heptane / -10 - 20 °C

3: 84 percent / H₂SO₄; AcOH / 0.5 h / 20 °C

4: 98 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

5: 30 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂; diethyl ether / -40 - 20 °C

6: 75 percent / NaOAc / palladium(II)chloride / acetic acid; H₂O / 40 - 45 °C

7: 69 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / -20 - 20 °C

With pyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In diethyl ether; n-heptane; dichloromethane; water; acetic acid;

DOI:10.1081/CAR-100108276

Reference yield:

methyl 2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside (101068-98-8) → methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate trichloroacetimidate (406460-75-1)

Guidance literature:

Multi-step reaction with 6 steps

1: 64 percent / trifluoromethanesulfonic acid / CH₂Cl₂; heptane / -10 - 20 °C

2: 84 percent / H₂SO₄; AcOH / 0.5 h / 20 °C

3: 98 percent / BF₃*Et₂O / CH₂Cl₂ / 0 - 20 °C

4: 30 percent / molecular sieves 4 Angstroem; N-iodosuccinimide; trifluoromethanesulfonic acid / CH₂Cl₂; diethyl ether / -40 - 20 °C

5: 75 percent / NaOAc / palladium(II)chloride / acetic acid; H₂O / 40 - 45 °C

6: 69 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / -20 - 20 °C

With N-iodo-succinimide; trifluorormethanesulfonic acid; 4 A molecular sieve; sulfuric acid; boron trifluoride diethyl etherate; sodium acetate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium dichloride; In diethyl ether; n-heptane; dichloromethane; water; acetic acid;

DOI:10.1081/CAR-100108276

upstream raw materials:

trichloroacetonitrile

methyl (4-O-benzoyl-3-O-benzyl-2-O-acetyl-α-L-rhamnopyranosyl)-(1->4)-2,3-di-O-benzyl-α-D-galactopyranuronate

methyl 2,3-O-methylorthoacetyl-α-L-rhamnopyranoside

methyl 2-O-acetyl-4-O-benzoyl-α-L-rhamnopyranoside