[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

Base Information

Chemical Name:[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid
CAS No.:321667-26-9
Molecular Formula:C₄₁H₆₂O₇Si
Molecular Weight:695.025
Hs Code.:

[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

Synonyms:[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

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Chemical Property of [(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

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Technology Process of [(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

There total 19 articles about [(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid 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:

: 617715-17-0
2-((2R,4R,6R)-6-((S)-3-((2R,3S,6S)-6-((R,E)-2-acetoxy-6-methylhept-3-enyl)-3-methyltetrahydro-2H-pyran-2-yl)-2-methoxypropyl)-4-(tert-butyldiphenylsilyloxy)tetrahydro-2H-pyran-2-yl)acetic acid

: 321667-26-9
[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

Guidance literature:: With methanol; potassium carbonate; for 16h;
DOI:10.1002/anie.200351817

Reference yield:

: acetic acid (R)-(E)-1-((2S,5S,6R)-6-((S)-3-[(2R,4R,6R)-4-(tertbutyldiphenylsilanyloxy)-6-(2-oxoethyl)tetrahydropyran-2-yl]-2-methoxypropyl)-5-methyltetrahydropyran-2-ylmethyl)-5-methylhex-2-enyl ester

: 321667-26-9
[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

Guidance literature:: Multi-step reaction with 2 steps

1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

2: K₂CO₃; MeOH / 16 h

With methanol; sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene; potassium carbonate; In water; tert-butyl alcohol;
DOI:10.1002/anie.200351817

Reference yield:

: 617715-14-7
2-[(2S,5S,6R)-6-((S)-3-((2R,4S,6S)-4-(tert-butyldiphenylsilanyloxy)-6-[2-(4-methoxybenzyloxy)ethyl]-tetrahydropyran-2-yl)-2-methoxypropyl)-5-methyltetrahydropyran-2-yl]-ethanol

: 321667-26-9
[(2R,4R,6R)-6-((S)-3-[(2R,3R,6S)-6-((R)-(E)-2-hydroxy-6-methylhept-3-enyl)-3-methoxytetrahydropyran-2-yl]-2-methylpropyl)-4-(tert-butyldiphenylsilanyloxy)-tetrahydropyran-2-yl]acetic acid

Guidance literature:: Multi-step reaction with 9 steps

1.1: 95 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

2.1: Cp₂Zr(H)Cl / CH₂Cl₂ / 20 °C

2.2: dimethylzinc / CH₂Cl₂ / -78 °C

2.3: 87 percent / CH₂Cl₂ / 1 h / -78 - 0 °C

3.1: 75 percent / Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

4.1: (S)-2-methyloxazaborolidine; borane-tetrahydrofuran complex / -10 °C

5.1: 97 percent / pyridine; 4-(dimethylamino)pyridine / CH₂Cl₂

6.1: 100 percent / 2,3-dichloro-5,6-dicyano-1,4-benzoquinone / CH₂Cl₂; aq. phosphate buffer; 2-methyl-propan-2-ol / 1.5 h / pH 7

7.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂

8.1: NaClO₂; NaH₂PO₄; 2-methyl-2-butene / 2-methyl-propan-2-ol; H₂O / 0.75 h / 0 °C

9.1: K₂CO₃; MeOH / 16 h

With pyridine; methanol; dmap; sodium chlorite; sodium dihydrogenphosphate; Schwartz's reagent; borane-THF; (R)-2-methyl-oxazaborolidine; 2-methyl-but-2-ene; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; 2,3-dicyano-5,6-dichloro-p-benzoquinone; In phosphate buffer; dichloromethane; water; tert-butyl alcohol; 1.1: Dess-Martin oxidation / 3.1: Dess-Martin oxidation / 4.1: Corey-Bakshi-Shibata borohydride reduction / 7.1: Dess-Martin oxidation;
DOI:10.1002/anie.200351817