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

Base Information

• Chemical Name: 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
• CAS No.: 902751-30-8
• Molecular Formula: C₄₇H₄₂INO₆S
• Molecular Weight: 875.824
• Mol file: 902751-30-8.mol

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 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

There total 10 articles about 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 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: 62.0%

triethyl 2-(2-iodophenyl)orthoacetate (887699-73-2) + phenyl 2,7-di-O-benzyl-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside (902751-29-5) + trimethylsilyl cyanide (7677-24-9) → 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 (902751-30-8)

Guidance literature:

triethyl 2-(2-iodophenyl)orthoacetate; phenyl 2,7-di-O-benzyl-3-O-(2-naphthalenylmethyl)-D-glycero-α-D-thio-manno-heptopyranoside; With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 4h;

trimethylsilyl cyanide; With boron trifluoride diethyl etherate; In dichloromethane; 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) → 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 (902751-30-8)

Guidance literature:

Multi-step reaction with 5 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

With osmium(VIII) oxide; oxalyl dichloride; bis-(2-chloro-ethyl)-methyl-amine oxide; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; trifluoroacetic acid; In dichloromethane; water; acetone; toluene; tert-butyl alcohol;

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) → 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 (902751-30-8)

Guidance literature:

Multi-step reaction with 3 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

With osmium(VIII) oxide; bis-(2-chloro-ethyl)-methyl-amine oxide; camphor-10-sulfonic acid; trifluoroacetic acid; In dichloromethane; water; acetone; tert-butyl alcohol;

DOI:10.1021/ja061594u

upstream raw materials:

triethyl 2-(2-iodophenyl)orthoacetate

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

trimethylsilyl cyanide

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

Downstream raw materials:

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

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