(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

Base Information

Chemical Name:(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one
CAS No.:373620-58-7
Molecular Formula:C₃₅H₄₂O₄S₂
Molecular Weight:590.848
Hs Code.:

Synonyms:(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

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Chemical Property of (+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

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Technology Process of (+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

There total 6 articles about (+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one 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: 42.0%

: 373620-57-6
(+/-)-2,4-bis(benzyloxy)-6-(5-(2-(4-hydroxypentyl)-1,3-dithian-2-yl)-pentyl)-benzoic acid

: 373620-58-7
(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

Guidance literature:: With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; toluene;
DOI:10.1007/s007060170067

Reference yield:

: 112185-22-5
5-(tert-butyldimethylsilanyloxy)hexanal

: 373620-58-7
(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

Guidance literature:: Multi-step reaction with 6 steps

1.1: Mg; I₂ / diethyl ether / 1 h / Heating

1.2: 54 percent / diethyl ether / 1 h / 20 °C

2.1: 72 percent / oxalyl chloride; DMSO; NEt₃ / CH₂Cl₂ / -70 - 20 °C

3.1: 39 percent / BF₃*Et₂O / methanol / 0 - 20 °C

4.1: BBN / tetrahydrofuran / 0 - 20 °C

4.2: 55 percent / K₃PO₄ / Pd(PPh₃)4 / dioxane; H₂O; tetrahydrofuran / 16 h / 95 °C

5.1: 95 percent / aq. KOH / ethanol / 30 h / Heating

6.1: 42 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran

With potassium hydroxide; oxalyl dichloride; BBN; boron trifluoride diethyl etherate; iodine; magnesium; dimethyl sulfoxide; triethylamine; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; methanol; diethyl ether; ethanol; dichloromethane; toluene; 1.2: Grignard reaction / 2.1: Swern oxidation / 6.1: Mitsunobu reaction;
DOI:10.1007/s007060170067

Reference yield:

: 373620-55-4
(+/-)-2-(4-hydroxypentyl)-2-(4-pentenyl)-1,3-dithiane

: 373620-58-7
(+/-)-14,16-bis(benzyloxy)-3,4,5,6,7,8,9,10,11,12-decahydro-3-methyl-7,7-trimethylenedithio-2-benzoxacyclotetradecin-1-one

Guidance literature:: Multi-step reaction with 3 steps

1.1: BBN / tetrahydrofuran / 0 - 20 °C

1.2: 55 percent / K₃PO₄ / Pd(PPh₃)4 / dioxane; H₂O; tetrahydrofuran / 16 h / 95 °C

2.1: 95 percent / aq. KOH / ethanol / 30 h / Heating

3.1: 42 percent / diethyl azodicarboxylate; PPh₃ / toluene; tetrahydrofuran

With potassium hydroxide; BBN; triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; ethanol; toluene; 3.1: Mitsunobu reaction;
DOI:10.1007/s007060170067