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

Base Information

• Chemical Name: methyl 3-O-allyl-2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside
• CAS No.: 902751-21-7
• Molecular Formula: C₄₃H₅₀INO₁₁
• Molecular Weight: 883.775
• Mol file: 902751-21-7.mol

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

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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

There total 7 articles about methyl 3-O-allyl-2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside 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: 42.0%

phenyl 3-O-allyl-2,7-di-O-benyl-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-L-glycero-α-D-thio-manno-heptopyranoside (902751-19-3) + methyl 2,3-O-isopropylidene-α-L-rhamnoside (14133-63-2) → methyl 3-O-allyl-2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (902751-21-7)

Guidance literature:

phenyl 3-O-allyl-2,7-di-O-benyl-4,6-O-[1-cyano-2-(2-iodophenyl)ethylidene]-L-glycero-α-D-thio-manno-heptopyranoside; With trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; In dichloromethane; at -25 ℃; for 0.5h;

methyl 2,3-O-isopropylidene-α-L-rhamnoside; In dichloromethane; at -78 - 20 ℃; for 4h;

DOI:10.1021/ja061594u

Reference yield:

phenyl 3-O-allyl-2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-thiomannopyranoside (902751-14-8) → methyl 3-O-allyl-2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (902751-21-7)

Guidance literature:

Multi-step reaction with 4 steps

1.1: 89 percent / DIBAL-H / CH₂Cl₂; toluene / 3 h / 0 - 20 °C

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

2.2: SmI₂ / tetrahydrofuran / 1 h / 20 °C

2.3: TFA / CH₂Cl₂ / 2 h / 20 °C

3.1: CSA / CH₂Cl₂ / 18 h / 20 °C

3.2: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / -20 - 20 °C

4.1: DPSO; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -25 °C

4.2: 42 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

With oxalyl dichloride; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; toluene;

DOI:10.1021/ja061594u

Reference yield:

phenyl 3-O-allyl-2-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside (902751-15-9) → methyl 3-O-allyl-2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-L-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (902751-21-7)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: SmI₂ / tetrahydrofuran / 1 h / 20 °C

1.3: TFA / CH₂Cl₂ / 2 h / 20 °C

2.1: CSA / CH₂Cl₂ / 18 h / 20 °C

2.2: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / 4 h / -20 - 20 °C

3.1: DPSO; TTBP; Tf₂O / CH₂Cl₂ / 0.5 h / -25 °C

3.2: 42 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

With oxalyl dichloride; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; dimethyl sulfoxide; In dichloromethane;

DOI:10.1021/ja061594u

upstream raw materials:

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

methyl 2,3-O-isopropylidene-α-L-rhamnoside

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

phenyl 3-O-allyl-2,7-di-O-benzyl-L-glycero-α-D-thio-manno-heptopyranoside