Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Base Information

• Chemical Name: Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester
• CAS No.: 186448-81-7
• Molecular Formula: C₄₇H₇₆O₈S₃Si
• Molecular Weight: 893.399

Synonyms:Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Chemical Property of Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

Chemical Property:

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Technology Process of Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester

There total 13 articles about Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester 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: 85.0%

p-toluenesulfonyl chloride (98-59-9) + (E)-(2R,5R)-5-{2-[(2S,3R)-2-(4-Methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-ene-1,2-diol (186448-80-6) → Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-81-7)

Guidance literature:

With dmap; triethylamine; In dichloromethane; for 16h; Ambient temperature;

DOI:10.1021/ja963066w

Reference yield:

(1R,2R,4R)-4-<(phenylsulfonyl)methyl>-2-methoxy-1-<oxy>cyclohexane (127258-23-5) → Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-81-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) n-BuLi, 2.) BF₃*Et₂O, 3.) Na₂HPO₄, 4.) Na(Hg)

2: 92 percent / Et₃N

3: 87 percent / NaH / hexamethylphosphoric acid triamide / 6 h / Ambient temperature

4: 78 percent / LiI, BF₃*OEt₂ / diethyl ether / -78 °C

5: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

6: 87 percent / t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

7: 73 percent / camphorsulfonic acid / methanol / 2 h / Ambient temperature

8: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

With dmap; disodium hydrogenphosphate; n-butyllithium; sodium amalgam; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; sodium hydride; triethylamine; lithium iodide; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; dichloromethane;

DOI:10.1021/ja963066w

Reference yield:

O-(4-methoxybenzyl)-trichloroacetimidate (89238-99-3) → Toluene-4-sulfonic acid (E)-(2R,5R)-2-hydroxy-5-{2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-enyl ester (186448-81-7)

Guidance literature:

Multi-step reaction with 4 steps

1: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 °C

2: 87 percent / t-BuLi / hexamethylphosphoric acid triamide; tetrahydrofuran / -78 °C

3: 73 percent / camphorsulfonic acid / methanol / 2 h / Ambient temperature

4: 85 percent / Et₃N, DMAP / CH₂Cl₂ / 16 h / Ambient temperature

With dmap; camphor-10-sulfonic acid; boron trifluoride diethyl etherate; tert.-butyl lithium; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; dichloromethane;

DOI:10.1021/ja963066w

upstream raw materials:

p-toluenesulfonyl chloride

(E)-(2R,5R)-5-{2-[(2S,3R)-2-(4-Methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithian-2-yl}-3-methyl-hex-3-ene-1,2-diol

(1R,2R,4R)-4-<(phenylsulfonyl)methyl>-2-methoxy-1-<oxy>cyclohexane

O-(4-methoxybenzyl)-trichloroacetimidate

Downstream raw materials:

C₅₇H₁₀₀Br₂O₅S₄Si₂

2-[(E)-(1R,4R)-4-(tert-Butyl-dimethyl-silanyloxy)-5-iodo-1,3-dimethyl-pent-2-enyl]-2-[(2S,3R)-2-(4-methoxy-benzyloxy)-4-((1S,3R,4R)-3-methoxy-4-triisopropylsilanyloxy-cyclohexyl)-3-methyl-butyl]-[1,3]dithiane

C₅₈H₁₀₆O₇S₄Si₂

C₅₆H₁₀₀O₆S₄Si₂

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