N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

Base Information

Chemical Name:N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester
CAS No.:207107-99-1
Molecular Formula:C₄₅H₄₇NO₈
Molecular Weight:729.87
Hs Code.:

Synonyms:N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

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Chemical Property of N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

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Technology Process of N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

There total 7 articles about N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl 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: 71.0%

: 1877-71-0
benzene 1,3-dicarboxylic acid monomethyl ester

: (R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethylamine; hydrochloride

: 207107-99-1
N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

Guidance literature:: With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In chloroform; for 12h; Ambient temperature;
DOI:10.1016/S0040-4039(98)00342-6

Reference yield:

: 207107-96-8
2-Methyl-2-((2R,3R,4R,5R,6R)-3,4,5-tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-malonic acid

: 207107-99-1
N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 91 percent / Cu₂O / acetonitrile / 2 h / 80 °C

2: 82 percent / 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, NH₄HCO₃ / CHCl₃ / 12 h / Ambient temperature

3: Pb(OAc)4 / 2.5 h / 100 °C

4: 95 percent / HCl / ethyl acetate / 0.5 h / Ambient temperature

5: 71 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, DIPEA / CHCl₃ / 12 h / Ambient temperature

With lead(IV) acetate; hydrogenchloride; ammonium bicarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; copper(I) oxide; In chloroform; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4039(98)00342-6

Reference yield:

: 3879-79-6,17791-37-6,19488-61-0,53008-63-2,69237-94-1,69237-95-2,71526-33-5,83462-67-3,84799-77-9,103421-29-0,103421-30-3,139241-42-2,61330-62-9
(2R,3R,4S,5S,6S)-3,4,5-tris(benzyloxy)-2-((benzyloxy)methyl)-6-methoxytetrahydro-2H-pyran

: 207107-99-1
N-[(R)-1-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-benzyloxymethyl-tetrahydro-pyran-2-yl)-ethyl]-isophthalamic acid methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 96 percent / TMSOTf / acetonitrile / 18 h / Ambient temperature

2: NaOH / methanol / 3 h / 80 °C

3: 91 percent / Cu₂O / acetonitrile / 2 h / 80 °C

4: 82 percent / 2-ethoxy-1-ethoxycarbonyl-1,2-dihydroquinoline, NH₄HCO₃ / CHCl₃ / 12 h / Ambient temperature

5: Pb(OAc)4 / 2.5 h / 100 °C

6: 95 percent / HCl / ethyl acetate / 0.5 h / Ambient temperature

7: 71 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide, DIPEA / CHCl₃ / 12 h / Ambient temperature

With lead(IV) acetate; hydrogenchloride; sodium hydroxide; trimethylsilyl trifluoromethanesulfonate; ammonium bicarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline; N-ethyl-N,N-diisopropylamine; copper(I) oxide; In methanol; chloroform; ethyl acetate; acetonitrile;
DOI:10.1016/S0040-4039(98)00342-6