methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Base Information

Chemical Name:methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside
CAS No.:165199-13-3
Molecular Formula:C₅₁H₅₆O₁₂S
Molecular Weight:893.064
Hs Code.:

Synonyms:methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

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Chemical Property of methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

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Technology Process of methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

There total 5 articles about methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside 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: 86.0%

: 65827-59-0
2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl chloride

: 165199-14-4
methyl 4,6-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

: 165199-13-3
methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Guidance literature:: With 2,6-di-tert-butyl-4-methylpyridine; 4 Angstroem MS; silver trifluoromethanesulfonate; In dichloromethane; 1.) -15 deg C up to RT; 2.) RT, 90 min;
DOI:10.1002/(SICI)1099-0690(199906)1999:6<1367::AID-EJOC1367>3.0.CO;2-N

Reference yield:

: 1125-88-8
benzaldehyde dimethyl acetal

: 165199-13-3
methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / DL-camphorsulfonic acid / dimethylformamide / 7 h / 15 Torr / Ambient temperature

2: 50 percent / NaOH, Bu₄NHSO₄, H₂O / CH₂Cl₂ / 2 h / Heating

3: 1.) 2,6-di-tert-butyl-4-methylpyridine, AgOTf, molecular sieves 4 Angstroem / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, -15 deg C to r.t., 90 min

With sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; camphor-10-sulfonic acid; water; silver trifluoromethanesulfonate; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; N,N-dimethyl-formamide;
DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u

Reference yield:

: 165307-54-0
methyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside

: 165199-13-3
methyl O-(2-O-acetyl-3,4,6-tri-O-benzyl-α-D-mannopyranosyl)-(1->3)-4,6-O-benzylidene-2-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside

Guidance literature:: Multi-step reaction with 2 steps

1: 50 percent / NaOH, Bu₄NHSO₄, H₂O / CH₂Cl₂ / 2 h / Heating

2: 1.) 2,6-di-tert-butyl-4-methylpyridine, AgOTf, molecular sieves 4 Angstroem / 1.) CH₂Cl₂, 30 min, 2.) CH₂Cl₂, -15 deg C to r.t., 90 min

With sodium hydroxide; 2,6-di-tert-butyl-4-methylpyridine; 4 A molecular sieve; water; silver trifluoromethanesulfonate; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane;
DOI:10.1002/(sici)1521-3765(19981102)4:11<2182::aid-chem2182>3.0.co;2-u