methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

Base Information

Chemical Name:methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]
CAS No.:1442422-61-8
Molecular Formula:C₄₅H₅₀O₈S
Molecular Weight:750.953
Hs Code.:

methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

Synonyms:methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

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Chemical Property of methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

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Technology Process of methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

There total 10 articles about methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate] 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: 9.0%

: 67-56-1
methanol

: 1442422-58-3
(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenyl-methyl)-7-S-tris(thiophenol)-l-glycero-1-thia-α-D-thiomannoheptopyranoside

: 1442422-60-7
S-phenyl [(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranosylurinate]

: 1442422-61-8
methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

Guidance literature:: With copper(II) oxide; copper dichloride; In dichloromethane; water; at 20 ℃; for 4h; Inert atmosphere;
DOI:10.1016/j.tet.2013.04.094

Reference yield:

: 4163-65-9
per-O-acetyl-α-D-mannopyranose

: 1442422-60-7
S-phenyl [(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranosylurinate]

: 1442422-61-8
methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

Guidance literature:: Multi-step reaction with 9 steps

1.1: boron trifluoride diethyl etherate / dichloromethane / -78 - 20 °C / Inert atmosphere

2.1: sodium methylate / methanol / 20 °C / Inert atmosphere

3.1: toluene-4-sulfonic acid / N,N-dimethyl-formamide / 60 °C / Inert atmosphere

4.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux

4.2: 20 h / 20 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

5.2: 20 °C / Inert atmosphere

6.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - 20 °C / Inert atmosphere

7.1: oxalyl dichloride; dimethyl sulfoxide / tetrahydrofuran / 2 h / -60 - -40 °C / Inert atmosphere

7.2: 2 h / -78 - 20 °C / Inert atmosphere

8.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

8.2: -78 - 20 °C / Inert atmosphere

9.1: copper(II) oxide; copper dichloride / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; boron trifluoride diethyl etherate; sodium methylate; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; toluene-4-sulfonic acid; dimethyl sulfoxide; copper(II) oxide; copper dichloride; In tetrahydrofuran; methanol; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 7.1: |Swern Oxidation;
DOI:10.1016/j.tet.2013.04.094

Reference yield:

: 1442422-74-3
(2-methyl-5-tert-butylphenyl) 4,6-O-(p-methoxybenzylidene)-1-thia-α-D-mannopyranoside

: 1442422-60-7
S-phenyl [(2-methyl-5-tert-butylphenyl) 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-α-D-mannoheptopyranosylurinate]

: 1442422-61-8
methyl [(2-methyl-5-tertbutylphenyl)2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-1-thia-a-D-mannoheptopyranosyl urinate]

Guidance literature:: Multi-step reaction with 6 steps

1.1: di(n-butyl)tin oxide / toluene / Inert atmosphere; Reflux

1.2: 20 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide / 0.17 h / 0 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: diisobutylaluminium hydride / dichloromethane; toluene / 3 h / -78 - 20 °C / Inert atmosphere

4.1: oxalyl dichloride; dimethyl sulfoxide / tetrahydrofuran / 2 h / -60 - -40 °C / Inert atmosphere

4.2: 2 h / -78 - 20 °C / Inert atmosphere

5.1: n-butyllithium / tetrahydrofuran; hexane / 1.5 h / -78 °C / Inert atmosphere

5.2: -78 - 20 °C / Inert atmosphere

6.1: copper(II) oxide; copper dichloride / dichloromethane; water / 4 h / 20 °C / Inert atmosphere

With n-butyllithium; oxalyl dichloride; sodium hydride; diisobutylaluminium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; copper(II) oxide; copper dichloride; In tetrahydrofuran; hexane; dichloromethane; water; N,N-dimethyl-formamide; toluene; 4.1: |Swern Oxidation;
DOI:10.1016/j.tet.2013.04.094