Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester

Base Information

• Chemical Name: Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester
• CAS No.: 290300-54-8
• Molecular Formula: C₃₆H₅₇N₃O₁₅
• Molecular Weight: 771.86
• Mol file: 290300-54-8.mol

Synonyms:

Chemical Property of Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester

There total 6 articles about Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] 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:

2-[(2R,3S,4S,5R,6S)-2-Benzyloxymethyl-3,5-bis-(2-hydroxy-ethoxy)-6-methoxy-tetrahydro-pyran-4-yloxy]-ethanol (217460-63-4) → Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester (290300-54-8)

Guidance literature:

Multi-step reaction with 4 steps

1: HN₃; Ph₃P; DEAD / tetrahydrofuran

2: H₂ / Pd/C / ethanol

3: Et₃N / CH₂Cl₂

4: pyridine; DMAP

With pyridine; dmap; tris-(2-chloro-ethyl)-amine; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1: Mitsunobu reaction / 2: Reduction / 3: Condensation / 4: Acylation;

DOI:10.1016/S0960-894X(00)00251-1

Reference yield:

(2R,3S,4S,5R,6S)-3,4,5-Tris-(2-azido-ethoxy)-2-benzyloxymethyl-6-methoxy-tetrahydro-pyran (217460-64-5) → Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester (290300-54-8)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / Pd/C / ethanol

2: Et₃N / CH₂Cl₂

3: pyridine; DMAP

With pyridine; dmap; hydrogen; triethylamine; palladium on activated charcoal; In ethanol; dichloromethane; 1: Reduction / 2: Condensation / 3: Acylation;

DOI:10.1016/S0960-894X(00)00251-1

Reference yield:

((2R,3S,4S,5R,6S)-2-Benzyloxymethyl-3,5-bis-carboxymethoxy-6-methoxy-tetrahydro-pyran-4-yloxy)-acetic acid (217460-62-3) → Phthalic acid mono-[(2R,3S,4S,5R,6S)-3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl] ester (290300-54-8)

Guidance literature:

Multi-step reaction with 5 steps

1: BH₃ / tetrahydrofuran

2: HN₃; Ph₃P; DEAD / tetrahydrofuran

3: H₂ / Pd/C / ethanol

4: Et₃N / CH₂Cl₂

5: pyridine; DMAP

With pyridine; dmap; tris-(2-chloro-ethyl)-amine; borane; hydrogen; triethylamine; triphenylphosphine; diethylazodicarboxylate; palladium on activated charcoal; In tetrahydrofuran; ethanol; dichloromethane; 1: Reduction / 2: Mitsunobu reaction / 3: Reduction / 4: Condensation / 5: Acylation;

DOI:10.1016/S0960-894X(00)00251-1

upstream raw materials:

phthalic anhydride

{2-[(2R,3S,4S,5R,6S)-3,5-Bis-(2-tert-butoxycarbonylamino-ethoxy)-2-hydroxymethyl-6-methoxy-tetrahydro-pyran-4-yloxy]-ethyl}-carbamic acid tert-butyl ester

di-tert-butyl dicarbonate

[(2R,3S,4S,5R,6S)-3,4,5-Tris-(2-amino-ethoxy)-6-methoxy-tetrahydro-pyran-2-yl]-methanol

Downstream raw materials:

N,N-dioctadecyl-phthalamic acid 3,4,5-tris-(2-tert-butoxycarbonylamino-ethoxy)-6-methoxy-tetrahydro-pyran-2-ylmethyl ester