3-N-benzyloxycarbonylaminopropyl (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 (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside
CAS No.:212199-03-6
Molecular Formula:C₅₃H₆₁NO₁₃
Molecular Weight:920.066
Hs Code.:

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

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

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

There total 9 articles about 3-N-benzyloxycarbonylaminopropyl (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:

: 34637-22-4
3-[(N-benzyloxycarbonyl)amino]propanol

: 212199-03-6
3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 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

With 1,4-diaza-bicyclo[2.2.2]octane; 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

: 212199-03-6
3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 6 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

With 1,4-diaza-bicyclo[2.2.2]octane; 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-O-acetyl-4-O-benzyl-3-O-monochloroacetyl-1-thio-α-L-rhamnopyranoside

: 212199-03-6
3-N-benzyloxycarbonylaminopropyl (2,4,6-tri-O-benzyl-α-D-glucopyranosyl)-(1-3)-2-O-acetyl-4-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: 78 percent / mol. sieves 4A, NIS, TfOH / CH₂Cl₂; diethyl ether

2: 69 percent / AcOH, 2,6-lutidine, hydrazine dithiocarbonate / CH₂Cl₂; ethyl acetate

3: 34 percent / mol. sieves 4A, MeOTf / CH₂Cl₂; diethyl ether / 4 h / 0 °C

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

With 1,4-diaza-bicyclo[2.2.2]octane; 2,6-dimethylpyridine; N-iodo-succinimide; trifluorormethanesulfonic acid; RhCl(PPh₃)3; hydrazine dithiocarbonate; 4 A molecular sieve; acetic acid; methyl trifluoromethanesulfonate; mercury dichloride; mercury(II) oxide; In diethyl ether; dichloromethane; ethyl acetate;
DOI:10.1016/S0008-6215(97)10013-1