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

Base Information

• Chemical Name: phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside
• CAS No.: 902751-23-9
• Molecular Formula: C₃₈H₃₆O₆S
• Molecular Weight: 620.766
• Mol file: 902751-23-9.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 1 articles about phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside 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: 74.0%

benzyl bromide (100-39-0) + 2-bromomethylnaphthyl bromide (939-26-4) + phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside (808761-99-1) → phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-23-9)

Guidance literature:

phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside; With di(n-butyl)tin oxide; In toluene; for 4h; Heating;

2-bromomethylnaphthyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 8h;

benzyl bromide; With sodium hydride; In tetrahydrofuran; for 5h; Heating;

DOI:10.1021/ja061594u

Reference yield: 91.0%

phenyl 2-O-benzyl-4,6-O-(p-methoxybenzylidene)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-23-9) → phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-24-0)

Guidance literature:

With diisobutylaluminium hydride; In dichloromethane; toluene; at -20 - 20 ℃; for 3h;

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) → 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 (902751-36-4)

Guidance literature:

Multi-step reaction with 8 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

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

3.2: Bu₂SnO / toluene / 4 h / Heating

3.3: 59 percent / CsF / dimethylformamide / 10 h / 20 °C

4.1: 82 percent / TFA / CH₂Cl₂ / 2 h / 20 °C

5.1: CSA / CH₂Cl₂ / 4 h / 20 °C

5.2: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / -20 - 20 °C

6.1: DPSO; 2,4,6-tri-tert-butylpyrimidine; Tf₂O / CH₂Cl₂ / 0.5 h / -25 °C

6.2: 86 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

7.1: 57 percent / AIBN; Bu₃SnH / xylene / 2 h / Heating

8.1: 1-benzenesulfinyl piperidine; 2,4,6-tri-tert-butylpyridmidine; Tf₂O / CH₂Cl₂ / 0.33 h / -60 °C

8.2: 88 percent / CH₂Cl₂ / 5 h / -60 - 20 °C

With osmium(VIII) oxide; oxalyl dichloride; 1-benzenesulfinyl piperidine; 2,2'-azobis(isobutyronitrile); bis-(2-chloro-ethyl)-methyl-amine oxide; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; tri-n-butyl-tin hydride; diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic acid; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; acetone; toluene; xylene; tert-butyl alcohol;

DOI:10.1021/ja061594u

upstream raw materials:

benzyl bromide

2-bromomethylnaphthyl bromide

phenyl 4,6-O-p-methoxybenzylidene-1-thio-α-D-mannopyranoside

Downstream raw materials:

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-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