(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

Base Information

Chemical Name:(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid
CAS No.:905312-35-8
Molecular Formula:C₄₀H₅₆O₁₁SSi
Molecular Weight:773.03
Hs Code.:

(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

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Chemical Property of (1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

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Technology Process of (1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

There total 11 articles about (1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic 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:

: Toluene-4-sulfonic acid (1R,2R)-1-[(1R,2S,3S,5R,6R)-3-benzyloxy-5-(tert-butyl-dimethyl-silanyloxy)-6-formyl-2-methoxymethoxy-cyclohexyl]-2-(4-methoxy-benzyloxy)-propyl ester

: 905312-35-8
(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

Guidance literature:: With sodium chlorite; sodium dihydrogenphosphate; amidosulfuric acid fluoride; In water; tert-butyl alcohol; at 20 ℃; for 12h;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-36-8
(2S,4R)-2-benzyloxy-4-(tert-butyldimethylsilyloxy)-5-hydroxy-cyclohexan-1-one

: 905312-35-8
(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 7 steps

1.1: MsCl; Et₃N / CH₂Cl₂ / 2.5 h / 0 °C

1.2: 3.50 g / HCl / H₂O

2.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

2.2: diethyl ether / 0.5 h / -78 °C

2.3: 85 percent / diethyl ether / 0.33 h / -78 °C

3.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

4.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

5.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

6.1: ozone / methanol / 0.08 h / -78 °C

6.2: Me₂S / methanol / 12 h / -78 - 20 °C

7.1: 6.1 mg / NaH₂PO₄*H₂O; HOSO₂NH₂; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; amidosulfuric acid fluoride; copper(l) cyanide; ozone; acetic acid; methanesulfonyl chloride; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; hexane; dichloromethane; water; 1,2-dichloro-ethane; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.04.079

Reference yield:

: 581060-33-5
(4R,6S)-6-benzyloxy-4-[(tert-butyldimethylsilyl)oxy]-2-cyclohexenone

: 905312-35-8
(1R,2R,3S,4S,6R)-4-Benzyloxy-6-(tert-butyl-dimethyl-silanyloxy)-2-[(1R,2R)-2-(4-methoxy-benzyloxy)-1-(toluene-4-sulfonyloxy)-propyl]-3-methoxymethoxy-cyclohexanecarboxylic acid

Guidance literature:: Multi-step reaction with 6 steps

1.1: copper(I) cyanide / diethyl ether / -78 - 0 °C

1.2: diethyl ether / 0.5 h / -78 °C

1.3: 85 percent / diethyl ether / 0.33 h / -78 °C

2.1: 70 percent / Me₄NBH(OAc)3; acetic acid / tetrahydrofuran / 24 h / 0 - 20 °C

3.1: 100 percent / BuLi / tetrahydrofuran; hexane / 0.33 h / 0 °C

4.1: 98 percent / i-Pr₂NEt / 1,2-dichloro-ethane / 3.5 h / 50 °C

5.1: ozone / methanol / 0.08 h / -78 °C

5.2: Me₂S / methanol / 12 h / -78 - 20 °C

6.1: 6.1 mg / NaH₂PO₄*H₂O; HOSO₂NH₂; NaClO₂ / 2-methyl-propan-2-ol; H₂O / 12 h / 20 °C

With sodium chlorite; sodium dihydrogenphosphate; n-butyllithium; amidosulfuric acid fluoride; copper(l) cyanide; ozone; acetic acid; N-ethyl-N,N-diisopropylamine; tetramethylammonium triacetoxyborohydride; In tetrahydrofuran; methanol; diethyl ether; hexane; water; 1,2-dichloro-ethane; tert-butyl alcohol;
DOI:10.1016/j.tet.2006.04.079