benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

Base Information

Chemical Name:benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside
CAS No.:861695-56-9
Molecular Formula:C₅₅H₅₃NO₁₃
Molecular Weight:936.025
Hs Code.:

Synonyms:benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

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Chemical Property of benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

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Technology Process of benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

There total 7 articles about benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside 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: 85.0%

: 861695-55-8
benzyl O-(2-O-benzoyl-4,6-O-benzylidene-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

: 861695-56-9
benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

Guidance literature:: With borane-THF; copper(II) bis(trifluoromethanesulfonate); In tetrahydrofuran; dichloromethane; at 20 ℃; for 2h; regioselective reaction; Inert atmosphere;
DOI:10.1016/j.bmc.2013.03.009

Reference yield:

: Acetic acid (2R,4aR,6S,7R,8S,8aR)-6-ethylsulfanyl-8-(4-methoxy-benzyloxy)-2-phenyl-hexahydro-pyrano[3,2-d][1,3]dioxin-7-yl ester

: 861695-56-9
benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 6 steps

1: 74 percent / NIS; AgOTf; molecular sieves 4 Angstroem / CH₂Cl₂ / -40 - 20 °C

2: NaOMe / methanol / 8 h / 20 °C

3: pyridine / CH₂Cl₂ / 0 °C

4: 140 mg / toluene / 2 h / Heating

5: 75 percent / DDQ; H₂O / CH₂Cl₂ / 9 h

6: 78 percent / BH₃; Bu₂BOTf / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

With pyridine; N-iodo-succinimide; 4 A molecular sieve; di-n-butylboryl trifluoromethanesulfonate; borane; water; sodium methylate; silver trifluoromethanesulfonate; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; methanol; dichloromethane; toluene;
DOI:10.1021/ja051715a

Reference yield:

: benzyl [4,6-O-benzylidine-3-O-p-methoxybenzyl-β-D-glucopyranosyl]-(1→4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

: 861695-56-9
benzyl O-(2-O-benzoyl-4-O-benzyl-β-D-mannopyranosyl)-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalamido-β-D-glucopyranoside

Guidance literature:: Multi-step reaction with 4 steps

1: pyridine / CH₂Cl₂ / 0 °C

2: 140 mg / toluene / 2 h / Heating

3: 75 percent / DDQ; H₂O / CH₂Cl₂ / 9 h

4: 78 percent / BH₃; Bu₂BOTf / tetrahydrofuran; CH₂Cl₂ / 3 h / 0 °C

With pyridine; di-n-butylboryl trifluoromethanesulfonate; borane; water; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In tetrahydrofuran; dichloromethane; toluene;
DOI:10.1021/ja051715a