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

Base Information

Chemical Name: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
CAS No.:902751-19-3
Molecular Formula:C₃₉H₃₈INO₆S
Molecular Weight:775.704
Hs Code.:

Synonyms: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

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Chemical Property of 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

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Technology Process of 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

There total 6 articles about 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 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%

: 887699-73-2
triethyl 2-(2-iodophenyl)orthoacetate

: 902751-17-1
phenyl 3-O-allyl-2,7-di-O-benzyl-L-glycero-α-D-thio-manno-heptopyranoside

: 7677-24-9
trimethylsilyl cyanide

: 902751-19-3
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

Guidance literature:: triethyl 2-(2-iodophenyl)orthoacetate; phenyl 3-O-allyl-2,7-di-O-benzyl-L-glycero-α-D-thio-manno-heptopyranoside; With camphor-10-sulfonic acid; In dichloromethane; at 20 ℃; for 18h;

trimethylsilyl cyanide; With boron trifluoride diethyl etherate; In dichloromethane; at -20 - 20 ℃; for 4h;
DOI:10.1021/ja061594u

Reference yield:

: 902751-15-9
phenyl 3-O-allyl-2-O-benzyl-4-O-(p-methoxybenzyl)-α-D-thiomannopyranoside

: 902751-19-3
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

Guidance literature:: Multi-step reaction with 2 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

With oxalyl dichloride; camphor-10-sulfonic acid; dimethyl sulfoxide; In dichloromethane;
DOI:10.1021/ja061594u

Reference yield:

: 902751-14-8
phenyl 3-O-allyl-2-O-benzyl-4,6-O-(p-methoxybenzylidene)-α-D-thiomannopyranoside

: 902751-19-3
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

Guidance literature:: Multi-step reaction with 3 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

With oxalyl dichloride; camphor-10-sulfonic acid; diisobutylaluminium hydride; dimethyl sulfoxide; In dichloromethane; toluene;
DOI:10.1021/ja061594u