2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Base Information

Chemical Name:2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside
CAS No.:1384443-02-0
Molecular Formula:C₅₂H₆₅NO₁₅
Molecular Weight:944.086
Hs Code.:

Synonyms:2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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Chemical Property of 2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

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Technology Process of 2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

There total 8 articles about 2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-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: 70.0%

: 1384443-01-9
2-[(N-benzyloxycarbonyl)amino]ethyl 2,4-di-O-acetyl-3-O-allyl-α-L-rhamnopyranosyl-(1->3)-2-O-benzoyl-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

: 1384443-02-0
2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: With sodium methylate; In methanol; at 20 ℃; for 1h;
DOI:10.1016/j.carres.2012.01.007

Reference yield:

: 1384442-63-0
2-methyl-5-tert-butylphenyl 1-thio-L-rhamnopyranoside

: 1384443-02-0
2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 10 steps

1.1: camphor-10-sulfonic acid / acetonitrile / 12 h / 20 °C

1.2: 2 h / 0 - 20 °C

2.1: sodium methylate / methanol / 1 h / 20 °C

3.1: di(n-butyl)tin oxide / methanol / 6 h / Reflux; Inert atmosphere

3.2: 48 h / 90 °C

4.1: pyridine / 12 h / 0 - 20 °C

5.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

6.1: sodium methylate / methanol / 20 °C

7.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

8.1: tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; thiourea / tetrahydrofuran / 12 h / 55 °C

9.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

10.1: sodium methylate / methanol / 1 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; sodium hydrogencarbonate; thiourea; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.carres.2012.01.007

Reference yield:

: 2-methyl-5-tert-butylphenyl 2,3,4-tri-O-acetyl-1-thio-L-rhamnopyranoside

: 1384443-02-0
2-[(N-benzyloxycarbonyl)amino]ethyl 3-O-allyl-α-L-rhamnopyranosyl-(1->3)-4-O-benzyl-α-L-rhamnopyranosyl-(1->2)-3,4-di-O-benzyl-α-L-rhamnopyranoside

Guidance literature:: Multi-step reaction with 11 steps

1.1: sodium methylate / methanol / 1 h / 20 °C

2.1: camphor-10-sulfonic acid / acetonitrile / 12 h / 20 °C

2.2: 2 h / 0 - 20 °C

3.1: sodium methylate / methanol / 1 h / 20 °C

4.1: di(n-butyl)tin oxide / methanol / 6 h / Reflux; Inert atmosphere

4.2: 48 h / 90 °C

5.1: pyridine / 12 h / 0 - 20 °C

6.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

7.1: sodium methylate / methanol / 20 °C

8.1: N-iodo-succinimide; silver trifluoromethanesulfonate / dichloromethane / 0.5 h / 20 °C / Molecular sieve; Inert atmosphere

9.1: tetra-(n-butyl)ammonium iodide; sodium hydrogencarbonate; thiourea / tetrahydrofuran / 12 h / 55 °C

10.1: trimethylsilyl trifluoromethanesulfonate / dichloromethane / 0.5 h / 0 °C / Molecular sieve; Inert atmosphere

11.1: sodium methylate / methanol / 1 h / 20 °C

With N-iodo-succinimide; trimethylsilyl trifluoromethanesulfonate; camphor-10-sulfonic acid; sodium methylate; silver trifluoromethanesulfonate; tetra-(n-butyl)ammonium iodide; di(n-butyl)tin oxide; sodium hydrogencarbonate; thiourea; In tetrahydrofuran; pyridine; methanol; dichloromethane; acetonitrile;
DOI:10.1016/j.carres.2012.01.007