(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

Base Information

Chemical Name:(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol
CAS No.:273733-98-5
Molecular Formula:C₃₁H₄₂O₇S
Molecular Weight:558.736
Hs Code.:

Synonyms:(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

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Chemical Property of (2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

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Technology Process of (2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

There total 14 articles about (2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol 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:

: 34097-60-4
methyl benzenesulfonylacetate

: 273733-98-5
(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

Guidance literature:: Multi-step reaction with 3 steps

1.1: 83 percent / NaH / ethanol / 12 h / 23 °C

2.1: NaH / dimethylformamide / 0.25 h / 23 °C

2.2: 91 percent / dimethylformamide / 12.25 h / 23 - 60 °C

3.1: LiBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

With lithium borohydride; sodium hydride; In tetrahydrofuran; ethanol; N,N-dimethyl-formamide; 1.1: Substitution / 2.1: Metallation / 2.2: Alkylation / 3.1: Reduction;
DOI:10.1016/S0040-4039(00)00158-1

Reference yield:

: 273733-97-4
(3S,5S)-3-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-3-benzenesulfonyl-5-(4-methoxy-benzyloxymethyl)-dihydro-furan-2-one

: 273733-98-5
(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

Guidance literature:: With lithium borohydride; In tetrahydrofuran; at 0 - 23 ℃; for 12h;
DOI:10.1016/S0040-4039(00)00158-1

Reference yield:

: 90865-70-6
[3R]-4-Benzyloxy-3-methylbutanal

: 273733-98-5
(2S,4S)-2-[(R)-3-((2R,6R)-6-Allyl-3,6-dihydro-2H-pyran-2-yl)-2-methyl-propyl]-2-benzenesulfonyl-5-(4-methoxy-benzyloxy)-pentane-1,4-diol

Guidance literature:: Multi-step reaction with 10 steps

1.1: 75 percent / tetrahydrofuran / -100 °C

2.1: 76 percent / triethylamine / CH₂Cl₂ / 0 - 23 °C

3.1: 72 percent / Ti(OiPr)4 / Cl₂(PCy₃)2Ru=CHPh / CH₂Cl₂ / 5 h / 40 °C

4.1: DIBAL-H / CH₂Cl₂ / -78 °C

5.1: pyridine; DMAP / CH₂Cl₂ / -78 - 23 °C

6.1: 82 percent / BF₃*OEt₃ / CH₂Cl₂ / -78 °C

7.1: 78 percent / Li / liquid ammonia

8.1: 97 percent / I₂; PPh₃; imidazole / acetonitrile; diethyl ether

9.1: NaH / dimethylformamide / 0.25 h / 23 °C

9.2: 91 percent / dimethylformamide / 12.25 h / 23 - 60 °C

10.1: LiBH₄ / tetrahydrofuran / 12 h / 0 - 23 °C

With pyridine; 1H-imidazole; titanium(IV) isopropylate; dmap; lithium borohydride; boron trifluoride diethyl etherate; iodine; lithium; sodium hydride; diisobutylaluminium hydride; triethylamine; triphenylphosphine; Grubbs catalyst first generation; In tetrahydrofuran; diethyl ether; dichloromethane; ammonia; N,N-dimethyl-formamide; acetonitrile; 1.1: Alkylation / 2.1: Acylation / 3.1: Cyclization / 4.1: Reduction / 5.1: Acetylation / 6.1: Alkylation / 7.1: Elimination / 8.1: Iodination / 9.1: Metallation / 9.2: Alkylation / 10.1: Reduction;
DOI:10.1016/S0040-4039(00)00158-1