Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

Base Information

Chemical Name:Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester
CAS No.:855855-66-2
Molecular Formula:C₂₆H₂₈O₆S
Molecular Weight:468.571
Hs Code.:

Synonyms:Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

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Chemical Property of Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

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Technology Process of Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

There total 10 articles about Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl 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: 89.0%

: 855855-58-2
Benzoic acid (1S,3R)-3,4-dihydroxy-1-phenethyl-butyl ester

: 98-59-9
p-toluenesulfonyl chloride

: 855855-66-2
Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: With di(n-butyl)tin oxide; triethylamine; In dichloromethane; at 20 ℃;
DOI:10.1016/j.tetlet.2005.04.031

Reference yield:

: 855855-55-9
(3aR,5S,6aR)-2,2-Dimethyl-5-((E)-styryl)-tetrahydro-furo[2,3-d][1,3]dioxole

: 855855-66-2
Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

2: 72 percent / aq. AcOH / Heating

3: 92 percent / LiAlH₄ / tetrahydrofuran / 20 °C

4: 85 percent / CSA

5: 91 percent / DEAD; TPP / tetrahydrofuran

6: 74 percent / PTSA / methanol

7: 89 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; camphor-10-sulfonic acid; hydrogen; thiamine diphosphate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; triethylamine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; 5: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2005.04.031

Reference yield:

: 4613-68-7,14260-67-4,22248-90-4,74996-06-8
O¹,O²-isopropylidene-α-D-erythro-3-deoxy-pentodiald-1,4-ose

: 855855-66-2
Benzoic acid (1S,3R)-3-hydroxy-1-phenethyl-4-(toluene-4-sulfonyloxy)-butyl ester

Guidance literature:: Multi-step reaction with 8 steps

1: 67 percent / n-BuLi / tetrahydrofuran / 0 - 20 °C

2: 98 percent / H₂ / Raney-Ni / ethanol / 3102.89 Torr

3: 72 percent / aq. AcOH / Heating

4: 92 percent / LiAlH₄ / tetrahydrofuran / 20 °C

5: 85 percent / CSA

6: 91 percent / DEAD; TPP / tetrahydrofuran

7: 74 percent / PTSA / methanol

8: 89 percent / Bu₂SnO; triethylamine / CH₂Cl₂ / 20 °C

With lithium aluminium tetrahydride; n-butyllithium; camphor-10-sulfonic acid; hydrogen; thiamine diphosphate; di(n-butyl)tin oxide; toluene-4-sulfonic acid; acetic acid; triethylamine; diethylazodicarboxylate; nickel; In tetrahydrofuran; methanol; ethanol; dichloromethane; 1: Wittig olefination / 6: Mitsunobu reaction;
DOI:10.1016/j.tetlet.2005.04.031