(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

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Chemical Name:(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid
CAS No.:359773-61-8
Molecular Formula:C₂₉H₃₆NO₁₃P
Molecular Weight:637.577
Hs Code.:

Synonyms:(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

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Chemical Property of (R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

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Technology Process of (R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

There total 11 articles about (R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid 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: 95.0%

: 202464-67-3
di-O-benzyl 4,6-O-diacetyl-3-O-((R)-phenylsulfonylethylpropion-2-yl)-N-acetyl-α-D-glucosamine-1-phosphate

: 359773-61-8
(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

Guidance literature:: With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane; for 0.25h;
DOI:10.1021/ja016082o

Reference yield:

: 73089-68-6
benzyl 2-acetamido-4,6-O-benzylidene-3-O-[(R)-1-carboxyethyl]-2-deoxy-α-D-glucopyranoside

: 359773-61-8
(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

Guidance literature:: Multi-step reaction with 7 steps

1: 95 percent / EDCI; DMAP / CH₂Cl₂

2: aq. AcOH / Heating

3: pyridine

4: 53 percent / H₂; AcOH / Pd/C / 775.74 Torr

5: 1H-tetrazole / CH₂Cl₂ / 2 h

6: 760 mg / hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

7: 95 percent / DBU / CH₂Cl₂ / 0.25 h

With pyridine; 1H-tetrazole; dmap; hydrogen; dihydrogen peroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja016082o

Reference yield:

: 917029-90-4
benzyl 2-acetamido-2-deoxy-3-O-(D-1-{[2-(phenylsulfonyl)ethoxy]carbonyl}ethyl)-α-D-glucopyranoside

: 359773-61-8
(R)-2-[(2R,3S,4R,5R,6R)-3-Acetoxy-2-acetoxymethyl-5-acetylamino-6-(bis-benzyloxy-phosphoryloxy)-tetrahydro-pyran-4-yloxy]-propionic acid

Guidance literature:: Multi-step reaction with 5 steps

1: pyridine

2: 53 percent / H₂; AcOH / Pd/C / 775.74 Torr

3: 1H-tetrazole / CH₂Cl₂ / 2 h

4: 760 mg / hydrogen peroxide / tetrahydrofuran; H₂O / 1.5 h / 20 °C

5: 95 percent / DBU / CH₂Cl₂ / 0.25 h

With pyridine; 1H-tetrazole; hydrogen; dihydrogen peroxide; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; palladium on activated charcoal; In tetrahydrofuran; dichloromethane; water;
DOI:10.1021/ja016082o