Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Base Information

Chemical Name:Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside
CAS No.:331273-51-9
Molecular Formula:C₅₁H₅₆O₁₁
Molecular Weight:844.999
Hs Code.:

Synonyms:Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Chemical Property of Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

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Technology Process of Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

There total 7 articles about Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-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: 97.0%

: 108-24-7
acetic anhydride

: 331273-50-8
Methyl (3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 331273-51-9
Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: With pyridine; at 25 ℃; for 17h;
DOI:10.1055/s-2001-10800

Reference yield:

: 19488-48-3
methyl O-2,3,6-tri-O-benzyl-α-D-glucopyranoside

: 331273-51-9
Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH; 15-crown-5 / dimethylformamide / 1.5 h / 20 °C

1.2: dimethylformamide / 15 h / 50 °C

2.1: 0.72 g / Ac₂O; DMSO / 17 h / 25 °C

3.1: 56 percent / DBU / toluene / 1.5 h / 70 °C

4.1: 44 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 °C

5.1: 97 percent / pyridine / 17 h / 25 °C

With pyridine; sodium tetrahydroborate; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-2001-10800

Reference yield:

: 142789-96-6
1,2-O-anhydro-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranose

: 331273-51-9
Methyl (2-O-acetyl-3-O-benzyl-4,6-O-benzylidene-5a-carba-β-D-mannopyranosyl)-(1->4)-2,3,6-tri-O-benzyl-α-D-glucopyranoside

Guidance literature:: Multi-step reaction with 5 steps

1.1: NaH; 15-crown-5 / dimethylformamide / 1.5 h / 20 °C

1.2: dimethylformamide / 15 h / 50 °C

2.1: 0.72 g / Ac₂O; DMSO / 17 h / 25 °C

3.1: 56 percent / DBU / toluene / 1.5 h / 70 °C

4.1: 44 percent / NaBH₄ / CH₂Cl₂; methanol / 2 h / 0 °C

5.1: 97 percent / pyridine / 17 h / 25 °C

With pyridine; sodium tetrahydroborate; 15-crown-5; acetic anhydride; sodium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; dichloromethane; N,N-dimethyl-formamide; toluene;
DOI:10.1055/s-2001-10800