3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

Base Information

Chemical Name:3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid
CAS No.:865714-47-2
Molecular Formula:C₅₂H₆₉NO₈
Molecular Weight:836.122
Hs Code.:

Synonyms:3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

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Chemical Property of 3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

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Technology Process of 3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

There total 10 articles about 3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic 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: 87.0%

: 194980-13-7
3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid ethyl ester

: 865714-47-2
3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

Guidance literature:: With methanol; lithium hydroxide; In tetrahydrofuran; at 4 ℃; for 48h;
DOI:10.1021/ja970920q

Reference yield:

: 582-33-2
3-aminobenzoic acid ethyl ester

: 865714-47-2
3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

Guidance literature:: Multi-step reaction with 2 steps

1: 63 percent / EDC, HOBt, NMM / CH₂Cl₂ / 0 °C

2: 87 percent / LiOH, aq. MeOH / tetrahydrofuran / 48 h / 4 °C

With 4-methyl-morpholine; methanol; lithium hydroxide; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; In tetrahydrofuran; dichloromethane;
DOI:10.1021/ja970920q

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

: 865714-47-2
3-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-benzoic acid

Guidance literature:: Multi-step reaction with 8 steps

1: 1.) TMSOTf / 1.) CH₃CN, 0 deg C, overnight, 2.) 25 deg C

2: 95 percent / NaOMe / methanol / 2 h / 25 °C

3: 77 percent / NaH, nBu₄NI / dimethylformamide / 0 - 25 °C

4: 1.2173 g / OsO₄, NMO, tBuOH / acetone; H₂O / 16 h / 25 °C

5: 1.109 g / NaIO₄ / tetrahydrofuran; H₂O / 2 h

6: Jones reagent, Celite / acetone / 0 °C

7: 63 percent / EDC, HOBt, NMM / CH₂Cl₂ / 0 °C

8: 87 percent / LiOH, aq. MeOH / tetrahydrofuran / 48 h / 4 °C

With 4-methyl-morpholine; methanol; lithium hydroxide; sodium periodate; osmium(VIII) oxide; N-methyl-2-indolinone; jones reagent; trimethylsilyl trifluoromethanesulfonate; Celite; sodium methylate; tetra-(n-butyl)ammonium iodide; sodium hydride; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja970920q