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

Base Information

• Chemical Name: phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside
• CAS No.: 902751-27-3
• Molecular Formula: C₄₆H₄₆O₇S
• Molecular Weight: 742.933
• Mol file: 902751-27-3.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 9 articles about phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside 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: 59.0%

phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside (902751-25-1) + benzyl bromide (100-39-0) → phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside (902751-27-3) + phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-L-glycero-α-D-thio-manno-heptopyranoside (902751-28-4)

Guidance literature:

phenyl 2-O-benzyl-6,7-dideoxy-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiohept-6-enopyranoside; With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; In water; acetone; tert-butyl alcohol; at 20 ℃; for 4h;

With di(n-butyl)tin oxide; In toluene; for 4h; Heating;

benzyl bromide; With cesium fluoride; In N,N-dimethyl-formamide; at 20 ℃; for 10h;

DOI:10.1021/ja061594u

Reference yield:

phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-6-O-(p-nitrobenzoyl)-D-glycero-α-D-thio-manno-heptopyranoside → phenyl 2,7-di-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside (902751-27-3)

Guidance literature:

With potassium carbonate; In methanol; dichloromethane; at 20 ℃; for 2h;

DOI:10.1021/ja061594u

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-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside (902751-27-3)

Guidance literature:

Multi-step reaction with 2 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

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

DOI:10.1021/ja061594u

upstream raw materials:

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

benzyl bromide

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

Downstream raw materials:

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

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

methyl 2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-D-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside

phenyl 2,7-di-O-benzyl-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-3-O-(2-naphthalenylmethyl)-L-glycero-α-D-thio-manno-heptopyranoside