Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Base Information

Chemical Name:Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester
CAS No.:419549-59-0
Molecular Formula:C₃₄H₄₁N₃O₇
Molecular Weight:603.715
Hs Code.:

Synonyms:Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

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Chemical Property of Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

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Technology Process of Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

There total 5 articles about Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl 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: 89.0%

: 170220-11-8
5-azido-1-pentanol

: 369386-67-4
ethyl 3-O-acetyl-2,4,6-tri-O-benzyl-1-thio-β-D-galactopyranoside

: 419549-59-0
Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: With 4 A molecular sieve; methyl trifluoromethanesulfonate; In diethyl ether; at 0 ℃; for 5h;
DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

: 213459-71-3
ethyl 2,6-di-O-benzyl-3,4-O-isopropylidene-1-thio-β-D-galactopyranoside

: 419549-59-0
Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 96 percent / aq. AcOH / 1 h / 60 °C

2: 76 percent / p-TsOH*H₂O / 0.1 h

3: 77 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.33 h

4: 96 percent / pyridine / 2 h

5: 89 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 5 h / 0 °C

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; toluene-4-sulfonic acid; acetic acid; methyl trifluoromethanesulfonate; In diethyl ether; dichloromethane;
DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C

Reference yield:

: 215371-44-1
ethyl 2,6-di-O-benzyl-1-thio-β-D-galactopyranoside

: 419549-59-0
Acetic acid (3R,4S,5S,6R)-2-(5-azido-pentyloxy)-3,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-4-yl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 76 percent / p-TsOH*H₂O / 0.1 h

2: 77 percent / LiAlH₄; AlCl₃ / diethyl ether; CH₂Cl₂ / 0.33 h

3: 96 percent / pyridine / 2 h

4: 89 percent / MeOTf; 4 Angstroem molecular sieves / diethyl ether / 5 h / 0 °C

With pyridine; lithium aluminium tetrahydride; aluminium trichloride; 4 A molecular sieve; toluene-4-sulfonic acid; methyl trifluoromethanesulfonate; In diethyl ether; dichloromethane;
DOI:10.1002/1521-3765(20020104)8:1<151::AID-CHEM151>3.0.CO;2-C