diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Base Information

Chemical Name:diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate
CAS No.:176590-52-6
Molecular Formula:C₃₄H₄₄NO₈P
Molecular Weight:625.699
Hs Code.:

Synonyms:diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

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Chemical Property of diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

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Technology Process of diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

There total 11 articles about diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate 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:

: 108-24-7
acetic anhydride

: ((2S,4R,5S,6R)-3-Amino-4,5-bis-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-ylmethyl)-phosphonic acid diethyl ester

: 176590-52-6
diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

: diethyl (((2S,3S,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: With dmap; In pyridine; for 1h;
DOI:10.1021/jo9519468

Reference yield:

: 160549-10-0
2,3,5-tri-O-benzyl-D-arabinofuranose

: 176590-52-6
diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: Multi-step reaction with 10 steps

1.1: zinc dibromide / tetrahydrofuran / 0.75 h / 0 - 20 °C / Inert atmosphere

1.2: 16 h / 0 - 20 °C / Inert atmosphere

2.1: mercury(II) diacetate / tetrahydrofuran / 16 h / 20 °C / Inert atmosphere

2.2: 0.5 h

3.1: iodine / dichloromethane / 16 h / Inert atmosphere

4.1: 2,6-dimethylpyridine / dichloromethane / 1 h / 0 - 20 °C / Inert atmosphere

5.1: 16 h / 160 °C / Sealed tube

6.1: trifluoroacetic acid; water / dichloromethane / 16 h / 0 - 20 °C

7.1: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C

8.1: acetic acid; hydroxylamine hydrochloride; sodium acetate / water; tetrahydrofuran; methanol / 1 h / pH 4.5

9.1: dmap; pyridine / dichloromethane / 16 h / 20 °C

10.1: borane-THF / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

10.2: 2 h / 0 - 50 °C

10.3: 16 h / 20 °C

With pyridine; 2,6-dimethylpyridine; dmap; borane-THF; hydroxylamine hydrochloride; mercury(II) diacetate; water; iodine; sodium acetate; acetic anhydride; acetic acid; trifluoroacetic acid; zinc dibromide; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;

Reference yield:

: 172223-08-4
diethyl (((2S,3R,4S,5R,6R)-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)-3-((tert-butyldimethylsilyl)oxy)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

: 176590-52-6
diethyl (((2S,3R,4R,5S,6R)-3-acetamido-4,5-bis(benzyloxy)-6-((benzyloxy)methyl)tetrahydro-2H-pyran-2-yl)methyl)phosphonate

Guidance literature:: Multi-step reaction with 5 steps

1.1: trifluoroacetic acid; water / dichloromethane / 16 h / 0 - 20 °C

2.1: acetic anhydride / dimethyl sulfoxide / 16 h / 20 °C

3.1: acetic acid; hydroxylamine hydrochloride; sodium acetate / water; tetrahydrofuran; methanol / 1 h / pH 4.5

4.1: dmap; pyridine / dichloromethane / 16 h / 20 °C

5.1: borane-THF / tetrahydrofuran / 16 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 - 50 °C

5.3: 16 h / 20 °C

With pyridine; dmap; borane-THF; hydroxylamine hydrochloride; water; sodium acetate; acetic anhydride; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; water; dimethyl sulfoxide;