phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside

Base Information

• Chemical Name: phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside
• CAS No.: 902751-31-9
• Molecular Formula: C₄₅H₄₂O₆S
• Molecular Weight: 710.891
• Mol file: 902751-31-9.mol

Synonyms:phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside

Chemical Property of phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside

There total 10 articles about phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside 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: 91.0%

phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside (1060735-41-2) + 2-bromomethylnaphthyl bromide (939-26-4) → phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside (902751-31-9)

Guidance literature:

phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-1-thio-α-D-mannoheptopyranoside; With sodium hydride; In N,N-dimethyl-formamide; mineral oil; for 0.333333h; Cooling with ice;

2-bromomethylnaphthyl bromide; With tetra-(n-butyl)ammonium iodide; In N,N-dimethyl-formamide; mineral oil; at 20 ℃; for 12.5h; Inert atmosphere; Darkness;

DOI:10.1021/jo801414c

Reference yield:

phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-24-0) → phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside (902751-31-9)

Guidance literature:

Multi-step reaction with 4 steps

1.1: oxalyl chloride; DMSO / CH₂Cl₂ / 1 h / -50 °C

1.2: NEt₃ / CH₂Cl₂ / 4 h / -50 - 20 °C

1.3: 64 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -40 °C

2.1: NMNO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 4 h / 20 °C

2.2: Bu₂SnO / toluene / 4 h / Heating

2.3: 59 percent / CsF / dimethylformamide / 10 h / 20 °C

3.1: 82 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

4.1: 89 percent / CSA / CH₂Cl₂ / 8 h / 20 °C

With osmium(VIII) oxide; oxalyl dichloride; bis-(2-chloro-ethyl)-methyl-amine oxide; camphor-10-sulfonic acid; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja061594u

Reference yield:

phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside (902751-25-1) → phenyl 2,7-di-O-benzyl-4,6-O-benzylidene-3-O-(2-naphthalenylmethyl)-D-glycero-1-thio-α-D-mannoheptopyranoside (902751-31-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: NMNO; OsO₄ / acetone; H₂O; 2-methyl-propan-2-ol / 4 h / 20 °C

1.2: Bu₂SnO / toluene / 4 h / Heating

1.3: 59 percent / CsF / dimethylformamide / 10 h / 20 °C

2.1: 82 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

3.1: 89 percent / CSA / CH₂Cl₂ / 8 h / 20 °C

With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; camphor-10-sulfonic acid; trifluoroacetic acid; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja061594u

upstream raw materials:

phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside

phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside

phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside

phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside

Downstream raw materials:

methyl 2,7-di-O-benzyl-4,6-O-benzylidene-D-glycero-β-D-manno-heptopyranosyl-(1->3)-2,7-di-O-benzyl-4-O-(2-cyanophenyl)acetyl-6-deoxy-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

phenyl 2,7-di-O-benzyl-4,6-O-benzylindene-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-mannoheptopyranosyl-(1-4)-2,3-O-(diphenylmethylene)-1-thio-α-L-rhamnopyranoside