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

Base Information

• Chemical Name: phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside
• CAS No.: 902751-25-1
• Molecular Formula: C₃₉H₃₈O₅S
• Molecular Weight: 618.794
• Mol file: 902751-25-1.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 5 articles about phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside 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: 64.0%

phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-24-0) + Methyltriphenylphosphonium bromide (1779-49-3) → phenyl 2-O-benzyl-4,6,7-trideoxy-3-O-(2-naphthalenylmethyl)-α-D-thiohept-4,6-dienopyranoside + phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside (902751-25-1)

Guidance literature:

phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside; With oxalyl dichloride; dimethyl sulfoxide; In dichloromethane; at -50 ℃; for 1h;

With triethylamine; In dichloromethane; at -50 - 20 ℃; for 4h;

Methyltriphenylphosphonium bromide; With n-butyllithium; In tetrahydrofuran; hexane; at -40 ℃; for 2h;

DOI:10.1021/ja061594u

Reference yield:

phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-23-9) → phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside (902751-25-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 91 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -20 - 20 °C

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

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

2.3: 64 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -40 °C

With oxalyl dichloride; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; toluene;

DOI:10.1021/ja061594u

Reference yield:

benzyl bromide (100-39-0) → phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside (902751-25-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: Bu₂SnO / toluene / 4 h / Heating

1.2: CsF / dimethylformamide / 8 h / 20 °C

1.3: 74 percent / NaH / tetrahydrofuran / 5 h / Heating

2.1: 91 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / -20 - 20 °C

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

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

3.3: 64 percent / n-BuLi / tetrahydrofuran; hexane / 2 h / -40 °C

With oxalyl dichloride; diisobutylaluminium hydride; di(n-butyl)tin oxide; dimethyl sulfoxide; In dichloromethane; toluene;

DOI:10.1021/ja061594u

upstream raw materials:

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

Methyltriphenylphosphonium bromide

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

benzyl bromide

Downstream raw materials:

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

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

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

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