3-N-benzyloxycarbonylaminopropyl (3-O-allyl-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-O-allyl-2,4-6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside
• CAS No.: 212199-02-5
• Molecular Formula: C₅₆H₆₅NO₁₃
• Molecular Weight: 960.131
• Mol file: 212199-02-5.mol

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

There total 8 articles about 3-N-benzyloxycarbonylaminopropyl (3-O-allyl-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: 34.0%

ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside (128716-38-1) + Acetic acid (2R,3R,4R,5R,6S)-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester (212199-01-4) → 3-N-benzyloxycarbonylaminopropyl (3-O-allyl-2,4-6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-02-5)

Guidance literature:

With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; dichloromethane; at 0 ℃; for 4h;

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

Reference yield:

3-[(N-benzyloxycarbonyl)amino]propanol (34637-22-4) → 3-N-benzyloxycarbonylaminopropyl (3-O-allyl-2,4-6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-02-5)

Guidance literature:

Multi-step reaction with 5 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

With 4 A molecular sieve; water; sodium methylate; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; 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-O-allyl-2,4-6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside (212199-02-5)

Guidance literature:

Multi-step reaction with 5 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

With 4 A molecular sieve; water; sodium methylate; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; In methanol; diethyl ether; dichloromethane; toluene;

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

upstream raw materials:

ethyl 3-O-allyl-2,4,6-tri-O-benzyl-1-thio-β-D-glucopyranoside

Acetic acid (2R,3R,4R,5R,6S)-5-benzyloxy-2-(3-benzyloxycarbonylamino-propoxy)-4-hydroxy-6-methyl-tetrahydro-pyran-3-yl ester

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:

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

C₆₅H₇₇NO₂₁

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