(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

Base Information

Chemical Name:(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester
CAS No.:155711-32-3
Molecular Formula:C₄₄H₆₂N₂O₈
Molecular Weight:746.985
Hs Code.:

(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

Synonyms:(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

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Chemical Property of (S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

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Technology Process of (S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

There total 7 articles about (S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl 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: 94.0%

: 155711-31-2
N-tetradecanoyl-O-<4,6-di-O-benzyl-2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl>-L-serine benzyl ester

: 155711-32-3
(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

Guidance literature:: With acetic acid; zinc; at 40 - 50 ℃; for 48h;
DOI:10.1248/cpb.41.1879

Reference yield:

: 81927-55-1
O-benzyl 2,2,2-trichloroacetimidate

: 155711-32-3
(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 20 h / Ambient temperature

2: 1.) 2)2>PF₆, H₂, 2.) iodine, pyridine / 1.) THF, 50 deg C, 2 h, 2.) THF, H₂O, RT, 15 min

3: thionyl bromide, DMF / CH₂Cl₂ / 5 h / Ambient temperature

4: 1.) 4 Angstroem molecular sieves, 2.) HgBr₂ / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 20 h

5: zinc / acetic acid / 16 h / 40 - 50 °C

With pyridine; sulfurous dibromide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; iodine; N,N-dimethyl-formamide; mercury dibromide; zinc; In dichloromethane; cyclohexane; acetic acid;
DOI:10.1248/cpb.44.2268

Reference yield:

: 134040-52-1
Allyl 2-deoxy-3-O-(2,2,2-trichloro-tert-butoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-α-D-glucopyranoside

: 155711-32-3
(S)-3-((2R,3R,4R,5S,6R)-3-Amino-5-benzyloxy-6-benzyloxymethyl-4-hydroxy-tetrahydro-pyran-2-yloxy)-2-tetradecanoylamino-propionic acid benzyl ester

Guidance literature:: Multi-step reaction with 5 steps

1: 62 percent / trifluoromethanesulfonic acid / CH₂Cl₂; cyclohexane / 20 h / Ambient temperature

2: 1.) 2)2>PF₆, H₂, 2.) iodine, pyridine / 1.) THF, 50 deg C, 2 h, 2.) THF, H₂O, RT, 15 min

3: thionyl bromide, DMF / CH₂Cl₂ / 5 h / Ambient temperature

4: 1.) 4 Angstroem molecular sieves, 2.) HgBr₂ / 1.) CH₂Cl₂, RT, 1 h, 2.) CH₂Cl₂, RT, 20 h

5: zinc / acetic acid / 16 h / 40 - 50 °C

With pyridine; dibromo sulfoxide; (1,5-cyclooctadiene)[bis(methyldiphenylphosphine)]iridium(I) hexafluorophosphate; trifluorormethanesulfonic acid; 4 A molecular sieve; hydrogen; iodine; N,N-dimethyl-formamide; mercury dibromide; zinc; In dichloromethane; cyclohexane; acetic acid;
DOI:10.1248/cpb.44.2268