((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

Base Information

Chemical Name:((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester
CAS No.:659721-28-5
Molecular Formula:C₂₁H₂₅O₈P
Molecular Weight:436.398
Hs Code.:

Synonyms:((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

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Chemical Property of ((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

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Technology Process of ((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

There total 3 articles about ((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester 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: 83.0%

: 659721-26-3
1,4-anhydro-1-(dibenzyloxyphosphoryl)methyl-2,3,6-tri-O-tert-butyldimethylsilyl-α-D-galactofuranose

: 659721-28-5
((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

Guidance literature:: With tetrabutyl ammonium fluoride; In tetrahydrofuran; at -5 ℃; for 16h;
DOI:10.1002/chem.200305141

Reference yield:

: 1-(dibenzyloxyphosphoryl)methyl-2,3,6-tri-O-tert-butyldimethylsilyl-D-galactofuranose

: 659721-28-5
((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 77 percent / pyridine; (CF₃CO)2O / tetrahydrofuran / 3 h / 0 °C

2: 74 percent / camphorsulfonic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / 17 h / Heating

3: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / -5 °C

With pyridine; 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; trifluoroacetic anhydride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200305141

Reference yield:

: 659721-21-8
(1(1')Z)-1-(dibenzyloxyphosphoryl)methylidene-2,3,6-tri-O-tert-butyldimethylsilyl-D-galactofuranose

: 659721-28-5
((1R,3R,4R,5R,6R)-5,6-Dihydroxy-3-hydroxymethyl-2,7-dioxa-bicyclo[2.2.1]hept-1-ylmethyl)-phosphonic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 74 percent / camphorsulfonic acid; 4 Angstroem molecular sieves / CH₂Cl₂ / 17 h / Heating

2: 83 percent / tetrabutylammonium fluoride / tetrahydrofuran / 16 h / -5 °C

With 4 A molecular sieve; camphor-10-sulfonic acid; tetrabutyl ammonium fluoride; In tetrahydrofuran; dichloromethane;
DOI:10.1002/chem.200305141