(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

Base Information

• Chemical Name: (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid
• CAS No.: 139277-16-0
• Molecular Formula: C₁₃H₁₄O₄S
• Molecular Weight: 266.318
• Mol file: 139277-16-0.mol

Synonyms:(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

Chemical Property of (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid

There total 1 articles about (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic 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: 82.0%

(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid (24363-23-3,38263-45-5,38263-46-6,64589-22-6,90760-55-7,90760-56-8,117772-64-2) + benzenesulfenyl chloride (931-59-9) → (1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (139277-16-0)

Guidance literature:

In chloroform; for 48h; 0 deg C to r.t.;

DOI:10.1021/jo00033a002

Reference yield: 90.0%

(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (139277-16-0) → (1R,2S,3R,4S,6R)-6-Hydroxymethyl-3-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptan-2-ol (139277-09-1)

Guidance literature:

With lithium aluminium tetrahydride; In tetrahydrofuran; at 0 ℃; for 1h;

DOI:10.1021/jo00033a002

Reference yield:

(1R,2S,4S,5R,6S)-6-Hydroxy-5-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptane-2-carboxylic acid (139277-16-0) → DL-(1,2,4/3,5)-5-hydroxymethyl-1,2,3,4-cyclohexanetetrol (10226-73-0,16656-62-5,16802-98-5,52079-85-3,64625-68-9,74560-71-7,74561-03-8,74561-07-2,74561-10-7,86117-80-8,86117-81-9,86117-82-0,90694-07-8,94943-08-5,94943-09-6,95043-48-4,96647-89-1,97372-13-9,97372-19-5,97372-28-6,97372-30-0,102629-13-0,105017-74-1,105017-81-0,108867-09-0,109668-67-9,135820-00-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 90 percent / LAH / tetrahydrofuran / 1 h / 0 °C

2: 90 percent / KOH / dioxane / 3 h / Heating

3: 97 percent / magnesium monoperoxyphthalate (MMPP) / methanol / 0 °C

4: 90 percent / n-BuLi, TMEDA / toluene; CH₂Cl₂ / 0.25 h / -78 °C

5: 88 percent / p-TsOH, 3A MS / CH₂Cl₂ / 36 h / Heating

6: 75 percent / Na(Hg), Na₂HPO₄, MeOH / 4 h / -20 deg C to r.t.

7: 95 percent / OsO₄, Me₃NO / acetone; H₂O / Ambient temperature

8: 90 percent / BF₃*OEt, EtSH / Ambient temperature

With methanol; potassium hydroxide; disodium hydrogenphosphate; osmium(VIII) oxide; lithium aluminium tetrahydride; n-butyllithium; sodium amalgam; N,N,N,N,-tetramethylethylenediamine; trimethylamine-N-oxide; boron trifluoride diethyl etherate; toluene-4-sulfonic acid; magnesium monoperoxyphthalate hexahydrate; ethanethiol; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; acetone; toluene;

DOI:10.1021/jo00033a002

upstream raw materials:

(+/-)-7-oxabicyclo[2.2.1]hept-5-ene-2-endo-carboxylic acid

benzenesulfenyl chloride

Downstream raw materials:

(1R,2S,3R,4S,6R)-6-Hydroxymethyl-3-phenylsulfanyl-7-oxa-bicyclo[2.2.1]heptan-2-ol

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

(4aR,8R,8aR)-8-Benzyloxy-4a,5,8,8a-tetrahydro-4H-benzo[1,3]dioxine

(4aR,6S,7S,8R,8aR)-8-Benzyloxy-hexahydro-benzo[1,3]dioxine-6,7-diol