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

Base Information

Chemical Name:(S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester
CAS No.:194980-11-5
Molecular Formula:C₆₄H₈₃NO₁₀
Molecular Weight:1026.36
Hs Code.:

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

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

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

There total 8 articles about (S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl 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: 73.0%

: 2791-84-6,227205-81-4
L-glutamic acid dibenzyl ester 4-toluenesulfonate

: 194980-03-5
((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetic acid

: 194980-11-5
(S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

Guidance literature:: With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; In dichloromethane; at 25 ℃; for 24h;
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

: 194980-11-5
(S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 7 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: 73 percent / HOBt, EDC, Et₃N / CH₂Cl₂ / 24 h / 25 °C

With 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; triethylamine; tert-butyl alcohol; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone;
DOI:10.1021/ja970920q

Reference yield:

: 112-82-3
hexadecanyl bromide

: 194980-11-5
(S)-2-[2-((2R,3R,4R,5R,6R)-3,4,5-Tris-benzyloxy-6-hexadecyloxymethyl-tetrahydro-pyran-2-yl)-acetylamino]-pentanedioic acid dibenzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 77 percent / NaH, nBu₄NI / dimethylformamide / 0 - 25 °C

2: 1.2173 g / OsO₄, NMO, tBuOH / acetone; H₂O / 16 h / 25 °C

3: 1.109 g / NaIO₄ / tetrahydrofuran; H₂O / 2 h

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

5: 73 percent / HOBt, EDC, Et₃N / CH₂Cl₂ / 24 h / 25 °C

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