<1S-<1α(4R,5S),3α,4β,5α,6α(2E,4R,6R),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Base Information

Chemical Name:<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)
CAS No.:170641-47-1
Molecular Formula:C₃₇H₄₇NO₁₂S
Molecular Weight:729.846
Hs Code.:

<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Synonyms:<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

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Chemical Property of <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

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Technology Process of <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

There total 5 articles about <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate) 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: 7.3%

: 170641-32-4
<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4,5-dimethyl ester

: 170641-47-1
<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

: <1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate), 4-methyl ester

Guidance literature:: With 2,4,6-trimethyl-pyridine; lithium iodide; at 45 - 50 ℃; for 45h;
DOI:10.1021/jm00018a010

Reference yield:

: 142561-97-5
zaragozic acid A trimethyl ester

: 170641-47-1
<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Guidance literature:: Multi-step reaction with 5 steps

1: aq. NaOH / tetrahydrofuran / 21 h

2: 1.) N-methylmorpholine, iBuOCOCl / 1.) THF, 2.) ether, 21 deg C, 2.5 h

3: 55 percent / 48percent aq. HBr / CHCl₃ / 2 h / 21 °C

4: 94 percent / ethanol; diethyl ether / 18 h / 21 °C

5: 32 percent / 2,4,6-collidine, LiI / 45 h / 45 - 50 °C

With 4-methyl-morpholine; 2,4,6-trimethyl-pyridine; sodium hydroxide; hydrogen bromide; lithium iodide; isobutyl chloroformate; In tetrahydrofuran; diethyl ether; ethanol; chloroform;
DOI:10.1021/jm00018a010

Reference yield:

: 144548-73-2
<1S-<1α-(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-3,4,5-tricarboxylic acid, 6-(4,6-dimethyl-6-octenoate), 4,5-dimethyl ester

: 170641-47-1
<1S-<1α(4R*,5S*),3α,4β,5α,6α(2E,4R*,6R*),7β>>-1-<4-(acetyloxy)-5-methyl-3-methylene-6-phenylhexyl>-3-(1,3-thiazol-4-yl)-4,6,7-trihydroxy-2,8-dioxabicyclo<3.2.1>octane-4,5-dicarboxylic acid, 6-(4,6-dimethyl-2-octenoate)

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) N-methylmorpholine, iBuOCOCl / 1.) THF, 2.) ether, 21 deg C, 2.5 h

2: 55 percent / 48percent aq. HBr / CHCl₃ / 2 h / 21 °C

3: 94 percent / ethanol; diethyl ether / 18 h / 21 °C

4: 32 percent / 2,4,6-collidine, LiI / 45 h / 45 - 50 °C

With 4-methyl-morpholine; 2,4,6-trimethyl-pyridine; hydrogen bromide; lithium iodide; isobutyl chloroformate; In diethyl ether; ethanol; chloroform;
DOI:10.1021/jm00018a010