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

Base Information

• Chemical Name: 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
• CAS No.: 902751-33-1
• Molecular Formula: C₄₀H₄₆INO₁₁
• Molecular Weight: 843.71
• Mol file: 902751-33-1.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 12 articles about 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 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: 84.0%

methyl 2,7-di-O-benzyl-4,6-O-{1-cyano-2-(2-iodophenyl)ethylidene}-3-O-(2-naphthalenylmethyl)-D-glycero-β-D-manno-heptopyranosyl-(1->4)-2,3-O-isopropylidene-α-L-rhamnopyranoside (902751-32-0) → 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 (902751-33-1)

Guidance literature:

With 2,3-dicyano-5,6-dichloro-p-benzoquinone; In dichloromethane; water; at 20 ℃; for 2h;

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) → 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 (902751-33-1)

Guidance literature:

Multi-step reaction with 5 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: CSA / CH₂Cl₂ / 4 h / 20 °C

3.2: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / -20 - 20 °C

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

4.2: 86 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

5.1: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja061594u

Reference yield:

phenyl 2-O-benzyl-4-O-(p-methoxybenzyl)-3-O-(2-naphthalenylmethyl)-α-D-thiomannopyranoside (902751-24-0) → 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 (902751-33-1)

Guidance literature:

Multi-step reaction with 6 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: CSA / CH₂Cl₂ / 4 h / 20 °C

4.2: 62 percent / BF₃*OEt₂ / CH₂Cl₂ / 3 h / -20 - 20 °C

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

5.2: 86 percent / CH₂Cl₂ / 4 h / -78 - 20 °C

6.1: 84 percent / DDQ / CH₂Cl₂; H₂O / 2 h / 20 °C

With osmium(VIII) oxide; oxalyl dichloride; bis-(2-chloro-ethyl)-methyl-amine oxide; trifluoromethylsulfonic anhydride; 1,1'-sulfinylbisbenzene; camphor-10-sulfonic acid; dimethyl sulfoxide; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; 2,4,6-tri-tert-butylpyrimidine; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja061594u

upstream raw materials:

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

triethyl 2-(2-iodophenyl)orthoacetate

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