methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate

Base Information

• Chemical Name: methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate
• CAS No.: 90413-94-8
• Molecular Formula: C₂₆H₂₂N₂O₇S₂
• Molecular Weight: 538.602

Synonyms:methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate

Chemical Property of methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate

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Technology Process of methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate

There total 3 articles about methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.0^2,7>undec-2(7)-ene-4-carboxylate 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: 19.0%

2,5-Bis<<(Z)-(2-nitrophenyl)sulfenyl>methylene>-3,6-dimethylene-7-oxabicyclo<2.2.1>heptane (98192-47-3) + acrylic acid methyl ester (292638-85-8,9003-21-8,96-33-3) → methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.02,7>undec-2(7)-ene-4-carboxylate (90413-94-8) + methyl (1RS,3SR,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.02,7>undec-2(7)-ene-4-carboxylate (90458-32-5)

Guidance literature:

at 70 ℃; for 15h;

DOI:10.1002/hlca.19850680815

Reference yield:

2,3,5,6-tetrakis(methylene)-7-oxabicyclo<2.2.1>heptane (53011-99-7) → methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.02,7>undec-2(7)-ene-4-carboxylate (90413-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LiCl, 2) t-BuOK / 1) 20 deg C, 3h, AcOH, 2) -78 to 20 deg C THF

2: neat (no solvent) / 15 h / 70 °C

With potassium tert-butylate; lithium chloride; In neat (no solvent);

DOI:10.1021/jo00187a046

Reference yield:

benzenesulfenyl chloride (931-59-9) → methyl (1RS,3RS,4RS,8RS)-10-methylidene-3-(2-nitrophenyl)sulfenyl-9-<(Z)-(2-nitrophenyl)sulfenylmethylidene>-11-oxatricyclo<6.2.1.02,7>undec-2(7)-ene-4-carboxylate (90413-94-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 1) LiCl, 2) t-BuOK / 1) 20 deg C, 3h, AcOH, 2) -78 to 20 deg C THF

2: neat (no solvent) / 15 h / 70 °C

With potassium tert-butylate; lithium chloride; In neat (no solvent);

DOI:10.1021/jo00187a046

upstream raw materials:

2,5-Bis<<(Z)-(2-nitrophenyl)sulfenyl>methylene>-3,6-dimethylene-7-oxabicyclo<2.2.1>heptane

acrylic acid methyl ester

2,3,5,6-tetrakis(methylene)-7-oxabicyclo<2.2.1>heptane

benzenesulfenyl chloride

Downstream raw materials:

methyl (1RS,2SR,5SR,6SR,9SR,10SR)-<2-acetyl-9,10-epoxy-1,2,3,4,5,6,7,8,9,10-decahydro-1,5-bis(2-nitrophenyl)sulfenyl-2-anthracene-6-carboxylate>

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