(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

Base Information

Chemical Name:(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester
CAS No.:188583-31-5
Molecular Formula:C₅₁H₆₉N₂O₁₂P
Molecular Weight:933.089
Hs Code.:

(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

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Chemical Property of (S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

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Technology Process of (S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

There total 13 articles about (S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric 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:

: 188583-30-4
N-tetradecanoyl-O-[6-O-benzyloxymethyl-2-deoxy-4-O-diphenoxyphosphoryl-3-O-(2,2,2-trichloroethoxycarbonyl)-2-(2,2,2-trichloroethoxycarbonylamino)-β-D-glucopyranosyl]-L-homoserine benzyl ester

: 188583-31-5
(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

Guidance literature:: With acetic acid; zinc; at 40 - 50 ℃; for 20h;
DOI:10.1248/cpb.45.312

Reference yield:

: 3587-60-8
Benzyloxymethyl chloride

: 188583-31-5
(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 4 steps

1: 71 percent / 1,1,3,3-tetramethylurea / CH₂Cl₂ / 24 h / Ambient temperature

2: 93 percent / pyridine, 4-dimethylaminopyridine / CH₂Cl₂ / 3 h / Ambient temperature

3: 60 percent / 4 A molecular sieves, N-bromosuccinimide, iodine, tetrabutylammonium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

4: Zn, AcOH / 20 h / 40 - 50 °C

With pyridine; dmap; N-Bromosuccinimide; 4 A molecular sieve; iodine; tetrabutylammonium trifluoromethylsulfonate; acetic acid; tetramethylurea; zinc; In dichloromethane;
DOI:10.1248/cpb.45.312

Reference yield:

: 100-39-0
benzyl bromide

: 188583-31-5
(S)-4-[(2R,3R,4R,5S,6R)-3-Amino-6-benzyloxymethoxymethyl-5-(diphenoxy-phosphoryloxy)-4-hydroxy-tetrahydro-pyran-2-yloxy]-2-tetradecanoylamino-butyric acid benzyl ester

Guidance literature:: Multi-step reaction with 3 steps

1: 81 percent / NaI / dimethylsulfoxide / 20 h / Ambient temperature

2: 60 percent / 4 A molecular sieves, N-bromosuccinimide, iodine, tetrabutylammonium trifluoromethanesulfonate / CH₂Cl₂ / 1 h / -20 °C

3: Zn, AcOH / 20 h / 40 - 50 °C

With N-Bromosuccinimide; 4 A molecular sieve; iodine; tetrabutylammonium trifluoromethylsulfonate; acetic acid; sodium iodide; zinc; In dichloromethane; dimethyl sulfoxide;
DOI:10.1248/cpb.45.312