3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Base Information

• Chemical Name: 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 212199-04-7
• Molecular Formula: C₆₈H₈₁NO₂₁
• Molecular Weight: 1248.39
• Mol file: 212199-04-7.mol

Synonyms:3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property of 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

There total 10 articles about 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-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: 52.0%

3,4,6-tri-O-acetyl-2-O-allyl-α,β-D-galactopyranosyl trichloroacetimidate (128716-35-8,128716-53-0) + 3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-03-6) → 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-04-7)

Guidance literature:

With trimethylsilyl trifluoromethanesulfonate; 4 A molecular sieve; In diethyl ether; at 0 ℃; for 1h;

DOI:10.1016/S0008-6215(97)10013-1

Reference yield:

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-04-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / mol. sieves 4A, TfOMe / CH₂Cl₂ / 18 h / Ambient temperature

2: NaOMe / methanol / 2 h

3: p-TsOH / toluene; CH₂Cl₂ / 0.5 h

4: H₂O, p-TsOH / toluene; CH₂Cl₂ / 0.33 h

5: 34 percent / mol. sieves 4A, MeOTf / CH₂Cl₂; diethyl ether / 4 h / 0 °C

6: 1) DABCO, RhCl(PPh₃)3, 2) HgO, HgCl₂ / 1) EtOH, toluene, H₂O, reflux, 3 h, 2) acetone, H₂O, 1 h

7: 52 percent / mol. sieves 4A, TMSOTf / diethyl ether / 1 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; trimethylsilyl trifluoromethanesulfonate; RhCl(PPh₃)3; 4 A molecular sieve; water; sodium methylate; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0008-6215(97)10013-1

Reference yield:

ethyl 2,3-di-O-acetyl-4-O-benzyl-1-thio-α-L-rhamnopyranoside → 3-N-benzyloxycarbonylaminopropyl (3,4,6-tri-O-acetyl-2-O-allyl-α-D-galactopyranosyl)-(1-3)-(2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-04-7)

Guidance literature:

Multi-step reaction with 7 steps

1: 81 percent / mol. sieves 4A, TfOMe / CH₂Cl₂ / 18 h / Ambient temperature

2: NaOMe / methanol / 2 h

3: p-TsOH / toluene; CH₂Cl₂ / 0.5 h

4: H₂O, p-TsOH / toluene; CH₂Cl₂ / 0.33 h

5: 34 percent / mol. sieves 4A, MeOTf / CH₂Cl₂; diethyl ether / 4 h / 0 °C

6: 1) DABCO, RhCl(PPh₃)3, 2) HgO, HgCl₂ / 1) EtOH, toluene, H₂O, reflux, 3 h, 2) acetone, H₂O, 1 h

7: 52 percent / mol. sieves 4A, TMSOTf / diethyl ether / 1 h / 0 °C

With 1,4-diaza-bicyclo[2.2.2]octane; trimethylsilyl trifluoromethanesulfonate; RhCl(PPh₃)3; 4 A molecular sieve; water; sodium methylate; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In methanol; diethyl ether; dichloromethane; toluene;

DOI:10.1016/S0008-6215(97)10013-1

upstream raw materials:

3,4,6-tri-O-acetyl-2-O-allyl-α,β-D-galactopyranosyl trichloroacetimidate

3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

3-[(N-benzyloxycarbonyl)amino]propanol

[3-((2R,3R,4S,5R,6S)-5-Benzyloxy-3,4-dihydroxy-6-methyl-tetrahydro-pyran-2-yloxy)-propyl]-carbamic acid benzyl ester

Downstream raw materials:

C₆₅H₇₇NO₂₁