Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Base Information

Chemical Name:Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester
CAS No.:116324-49-3
Molecular Formula:C₃₂H₃₉NO₁₃
Molecular Weight:645.661
Hs Code.:

Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Synonyms:Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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Chemical Property of Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

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Technology Process of Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

There total 6 articles about Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-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: 84.0%

: 116303-10-7
3-O-allyl-2-O-fluoromethyl-(R)-glyceric acid methyl ester

: 116303-11-8
Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-5-benzyloxycarbonylamino-3-hydroxy-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

: 116324-49-3
Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -20 ℃; for 1h; activated molecular sieve 4 Angstroem;
DOI:10.1016/S0040-4020(01)81477-0

Reference yield:

: 116303-08-3
3-O-allyl-2-O-methoxymethyl-(R)-glyceric acid methyl ester

: 116324-49-3
Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: acetic acid, trifluoroacetic acid / 1 h / Ambient temperature

2: 68 percent / 70percent HF/pyridine / CH₂Cl₂ / 0 °C

3: 84 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C / activated molecular sieve 4 Angstroem

With pyridine; boron trifluoride diethyl etherate; hydrogen fluoride; acetic acid; trifluoroacetic acid; In dichloromethane;
DOI:10.1016/S0040-4020(01)81477-0

Reference yield:

: 116303-09-4
2-O-acetoxymethyl-3-O-allyl-(R)-glyceric acid methyl ester

: 116324-49-3
Benzoic acid (2R,3S,4R,5R,6S)-4-acetoxy-3-((R)-2-allyloxy-1-methoxycarbonyl-ethoxymethoxy)-5-benzyloxycarbonylamino-6-methoxy-tetrahydro-pyran-2-ylmethyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 68 percent / 70percent HF/pyridine / CH₂Cl₂ / 0 °C

2: 84 percent / BF₃*Et₂O / CH₂Cl₂ / 1 h / -20 °C / activated molecular sieve 4 Angstroem

With pyridine; boron trifluoride diethyl etherate; hydrogen fluoride; In dichloromethane;
DOI:10.1016/S0040-4020(01)81477-0