a-D-Mannopyranoside, phenyl 3-O-[(4-Methoxyphenyl)Methyl]-2-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-

Base Information

• Chemical Name: a-D-Mannopyranoside, phenyl 3-O-[(4-Methoxyphenyl)Methyl]-2-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-
• CAS No.: 177943-74-7
• Molecular Formula: C34H34O6S
• Molecular Weight: 570.706
• Mol file: 177943-74-7.mol

Synonyms:phenyl 2-O-benzyl-3-O-p-methoxybenzyl-4,6-O-benzylidene-thio-α-D-mannopyranoside;phenyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside;mannosyl thioglycoside;(2R,4aR,6R,7S,8S,8aR)-7-Benzyloxy-8-(4-methoxy-benzyloxy)-2-phenyl-6-phenylsulfanyl-hexahydro-pyrano[3,2-d][1,3]dioxine;

Chemical Property of a-D-Mannopyranoside, phenyl 3-O-[(4-Methoxyphenyl)Methyl]-2-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-

Chemical Property:

• PSA: 80.68000
• LogP: 6.79720

Purity/Quality:

95% ^*data from raw suppliers

(R)-Phenyl3-O-[(4-methoxyphenyl)methyl]-2-O-(phenylmethyl)-4,6-O-(phenylmethylene)-1-thio-α-D-mannopyranoside ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: (R)-Phenyl 3-O-[(4-methoxyphenyl)methyl]-2-O-(phenylmethyl)-4,6-O-(phenylmethylene)-1-thio-α-D-mannopyranoside is used as a reactant in thd synthetic approach to the glycan chain of high mannose type N-glycoprotein.

Technology Process of a-D-Mannopyranoside, phenyl 3-O-[(4-Methoxyphenyl)Methyl]-2-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio-

There total 6 articles about a-D-Mannopyranoside, phenyl 3-O-[(4-Methoxyphenyl)Methyl]-2-O-(phenylMethyl)-4,6-O-[(R)-phenylMethylene]-1-thio- 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: 99.0%

benzyl bromide (100-39-0) + phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside (168138-26-9) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (177943-74-7)

Guidance literature:

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside; With sodium hydride; In N,N-dimethyl-formamide; at 0 ℃; for 0.166667h; Inert atmosphere;

benzyl bromide; In N,N-dimethyl-formamide; at 20 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.joc.0c01404

Reference yield:

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol (2936-70-1,5624-48-6,13992-15-9,16758-34-2,28244-97-5,77481-63-1,105088-17-3,149495-84-1,77481-62-0) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (177943-74-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 57 percent / p-TsOH / dimethylformamide / 2 h / 60 °C

2.1: Bu₂SnO / toluene / 3 h / Heating

2.2: 94 percent / Bu₄NBr; CsF / toluene / 3 h / Heating

3.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

3.2: 90 percent / tetrahydrofuran / Heating

With sodium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;

DOI:10.1021/ja0471931

Reference yield:

phenyl 4,6-O-benzylidene-1-thio-α-D-mannopyranoside (159407-19-9) → methyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-1-thio-α-D-mannopyranoside (177943-74-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: Bu₂SnO / toluene / 3 h / Heating

1.2: 94 percent / Bu₄NBr; CsF / toluene / 3 h / Heating

2.1: NaH / tetrahydrofuran / 0.5 h / 20 °C

2.2: 90 percent / tetrahydrofuran / Heating

With sodium hydride; di(n-butyl)tin oxide; In tetrahydrofuran; toluene;

DOI:10.1021/ja0471931

upstream raw materials:

benzyl bromide

phenyl 4,6-O-benzylidene-3-O-(4-methoxybenzyl)-1-thio-α-D-mannopyranoside

benzaldehyde dimethyl acetal

(2R,3S,4S,5S,6R)-2-Hydroxymethyl-6-phenylsulfanyl-tetrahydro-pyran-3,4,5-triol

Downstream raw materials:

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

2-O-benzyl-4,6-O-benzylidene-3-O-((4-methoxyphenyl)methyl)-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranosyl azide

benzyl 2-O-benzyl-4,6-O-benzylidene-3-O-p-methoxybenzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

benzyl 2-O-benzyl-3-O-p-methoxybenzyl-β-D-mannopyranosyl-(1->4)-3,6-di-O-benzyl-2-deoxy-2-phthalimido-β-D-glucopyranoside

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