(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

Base Information

Chemical Name:(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester
CAS No.:383125-03-9
Molecular Formula:C₂₉H₃₈O₅
Molecular Weight:466.618
Hs Code.:

Synonyms:(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

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Chemical Property of (R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

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Technology Process of (R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

There total 10 articles about (R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic 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: 45.0%

: 383125-12-0
(S)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

: 383125-03-9
(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

Guidance literature:: With sodium methylate; In methanol; at 60 ℃;
DOI:10.1016/S0040-4039(01)01657-4

Reference yield:

: 63914-23-8
3,6-di-O-acetyl-D-glucal

: 383125-03-9
(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 9 steps

1.1: i-Pr₂NEt / toluene / 20 °C

2.1: NH₃ / methanol / 40 °C

3.1: t-BuOK / dimethylformamide / 20 °C

4.1: Ph₃P*HBr / toluene / 20 °C

4.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 h / -78 °C

5.1: 84 percent / n-BuLi / tetrahydrofuran / 20 h / -78 °C

6.1: 80 percent / AcOH; water / 50 °C

7.1: 76 percent / toluene / 100 °C

8.1: 80 percent / MeONa / toluene / 70 °C

9.1: 45 percent / MeONa / methanol / 60 °C

With n-butyllithium; potassium tert-butylate; ammonia; water; sodium methylate; triphenylphosphine hydrobromide; acetic acid; N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 5.1: Wittig olefination / 7.1: Wittig reaction / 8.1: Michael reaction;
DOI:10.1016/S0040-4039(01)01657-4

Reference yield:

: 3,6-Di-O-acetyl-1,5-anhydro-4-O-(methoxymethyl)-2-deoxy-D-arabino-hex-1-enitol

: 383125-03-9
(R)-2-[(2S,4R,6S)-4-Benzyloxy-6-benzyloxymethyl-5-prop-(E)-ylidene-tetrahydro-pyran-2-yl]-pentanoic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: NH₃ / methanol / 40 °C

2.1: t-BuOK / dimethylformamide / 20 °C

3.1: Ph₃P*HBr / toluene / 20 °C

3.2: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / 0 h / -78 °C

4.1: 84 percent / n-BuLi / tetrahydrofuran / 20 h / -78 °C

5.1: 80 percent / AcOH; water / 50 °C

6.1: 76 percent / toluene / 100 °C

7.1: 80 percent / MeONa / toluene / 70 °C

8.1: 45 percent / MeONa / methanol / 60 °C

With n-butyllithium; potassium tert-butylate; ammonia; water; sodium methylate; triphenylphosphine hydrobromide; acetic acid; In tetrahydrofuran; methanol; N,N-dimethyl-formamide; toluene; 4.1: Wittig olefination / 6.1: Wittig reaction / 7.1: Michael reaction;
DOI:10.1016/S0040-4039(01)01657-4