(1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane

Base Information

• Chemical Name: (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane
• CAS No.: 112314-06-4
• Molecular Formula: C₂₀H₂₈O₇S
• Molecular Weight: 412.504

Synonyms:(1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane

Chemical Property of (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane

There total 9 articles about (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane 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: 94.0%

(1SR,2SR,6SR,7RS,9SR)-7-(hydroxymethyl)-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo<7.3.0.02,6>dodecane (90626-74-7,97372-23-1,114884-38-7,114884-39-8) + p-toluenesulfonyl chloride (98-59-9) → (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.02,6>dodecane (112314-06-4)

Guidance literature:

With pyridine; In dichloromethane; at 20 ℃;

DOI:10.1016/S0040-4039(00)00408-1

Reference yield:

(+/-)-(1S,2S,4S)-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-ol (64145-55-7,112460-49-8,123001-41-2) → (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.02,6>dodecane (112314-06-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / pyridine; DMAP / CH₂Cl₂ / 20 °C

2: 84 percent / OsO₄; NMMO / H₂O; acetone / 48 h / 20 °C

3: 90 percent / Amberlyst-15 / 20 °C

4: 70 percent / NaOMe / methanol / 3 h / 20 °C

5: 95 percent / OsO₄; NMMO / 30 h

6: 85 percent / Amberlyst-15; 4 Angstroem mol. sieves / 1 h / 20 °C

7: 82 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

8: 94 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; dmap; osmium(VIII) oxide; lithium aluminium tetrahydride; amberlyst-15; 4 A molecular sieve; sodium methylate; 4-methylmorpholine N-oxide; In tetrahydrofuran; methanol; dichloromethane; water; acetone; 1: Tosylation / 2: Oxidation / 3: Cyclization / 4: Isomerization / 5: Oxidation / 6: Cyclization / 7: Reduction / 8: Tosylation;

DOI:10.1016/S0040-4039(00)00408-1

Reference yield:

(3aS,4S,7aR)-2,2-Dimethyl-3a,4,5,7a-tetrahydro-benzo[1,3]dioxole-4-carboxylic acid methyl ester → (1RS,2RS,6SR,7RS,9RS)-4,4,11,11-tetramethyl-7-toluene-p-sulfonyloxy-3,5,10,12-tetraoxatricyclo<7.3.0.02,6>dodecane (112314-06-4)

Guidance literature:

Multi-step reaction with 4 steps

1: 95 percent / OsO₄; NMMO / 30 h

2: 85 percent / Amberlyst-15; 4 Angstroem mol. sieves / 1 h / 20 °C

3: 82 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

4: 94 percent / pyridine / CH₂Cl₂ / 20 °C

With pyridine; osmium(VIII) oxide; lithium aluminium tetrahydride; amberlyst-15; 4 A molecular sieve; 4-methylmorpholine N-oxide; In tetrahydrofuran; dichloromethane; 1: Oxidation / 2: Cyclization / 3: Reduction / 4: Tosylation;

DOI:10.1016/S0040-4039(00)00408-1

upstream raw materials:

(1SR,2SR,6SR,7RS,9SR)-7-(hydroxymethyl)-4,4,11,11-tetramethyl-3,5,10,12-tetraoxatricyclo<7.3.0.0^2,6>dodecane

p-toluenesulfonyl chloride

(+/-)-(1S,2S,4S)-7,7-dimethoxybicyclo[2.2.1]hept-5-en-2-ol

DL-(1,2/3,4,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol

Downstream raw materials:

DL-(1,2/3,4,5)-5-acetamidomethyl-1,2,3,4-tetra-O-acetyl-1,2,3,4-cyclohexanetetrol

DL-(1,2/3,4,5)-1,2,3,4-tetra-O-acetyl-5-methyl-1,2,3,4-cyclohexanetetrol

DL-(1,2/3,4,5)-1,2,3,4-tetra-O-acetyl-5-acethylthiomethyl-1,2,3,4-cyclohexanetetrol

DL-(1,2/3,4,5)-5-acetamidomethyl-1,2,3,4-cyclohexanetetrol

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