4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

Base Information

Chemical Name:4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol
CAS No.:605675-61-4
Molecular Formula:C₄₂H₄₆NO₇P
Molecular Weight:707.803
Hs Code.:

Synonyms:4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

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Chemical Property of 4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

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Technology Process of 4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

There total 15 articles about 4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol 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: 78.0%

: 605675-52-3
(2R,3R,4R,6S)-3,4-di(benzyloxy)-2-benzyloxymethyl-1-azabicyclo[4.1.0]heptane

: 1623-08-1
phosphoric acid dibenzyl ester

: 605675-61-4
4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

Guidance literature:: In dichloromethane; at 20 ℃;
DOI:10.1016/j.bmc.2004.12.043

Reference yield: 78.0%

: 1623-08-1
phosphoric acid dibenzyl ester

: (1R,2R,3R,4R,6S)-3,4-Bis-benzyloxy-2-benzyloxymethyl-1-aza-bicyclo[4.1.0]heptane

: 605675-61-4
4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

Guidance literature:: In dichloromethane; for 16h;
DOI:10.1016/S0957-4166(03)00364-1

Reference yield:

: 160549-11-1
3,4,6-tri-O-benzyl-2-deoxy-D-glucopyranose

: 605675-61-4
4,5,7-tri-O-benzyl-1-O-(dibenzyloxyphosphoryl)-2,3,6-trideoxy-2,6-imino-D-manno-heptitol

Guidance literature:: Multi-step reaction with 8 steps

1.1: BuLi / tetrahydrofuran; hexane / 1 h / 0 - 20 °C

1.2: 81 percent / hexane; tetrahydrofuran / 24 h / 20 °C

2.1: 87 percent / triphenylphosphine; diisopropyl azodicarboxylate / toluene / 20 °C

3.1: 91 percent / sodium / methanol / 4 h / 20 °C

4.1: 78 percent / triphenylphosphine; diisopropyl azodicarboxylate / toluene / 20 °C

5.1: ethylenediamine / ethanol / 80 °C

6.1: NIS / CH₂Cl₂ / 1 h / 20 °C

7.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / tetrahydrofuran / 5 h / Heating

8.1: 78 percent / CH₂Cl₂ / 20 °C

With N-iodo-succinimide; n-butyllithium; di-isopropyl azodicarboxylate; sodium; 1,8-diazabicyclo[5.4.0]undec-7-ene; ethylenediamine; triphenylphosphine; In tetrahydrofuran; methanol; ethanol; hexane; dichloromethane; toluene; 1.1: Wittig methylenation / 2.1: Mitsunobu reaction / 4.1: Mitsunobu reaction;
DOI:10.1016/j.bmc.2004.12.043