(6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

Base Information

• Chemical Name: (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl
• CAS No.: 154859-09-3
• Molecular Formula: C₂₂H₂₂O₂
• Molecular Weight: 318.415
• Mol file: 154859-09-3.mol

Synonyms:(6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

Chemical Property of (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl

There total 12 articles about (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl 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:

glutaric anhydride, (108-55-4) → (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl (154859-09-3)

Guidance literature:

Multi-step reaction with 4 steps

1: 66 percent / tetrahydrofuran; diethyl ether / 19 h / Ambient temperature

2: 97 percent / H₂SO₄ / 1 h

3: (4S,5R)-4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene, BH₃*DMS / tetrahydrofuran; toluene / 1 h / Ambient temperature

4: 1.) LHMDS, DMPU, 2.) N-phenyltrifluoromethanesulfonimide, 3.) LiCl, Sn₂Me₆, Pd(PPh₃)4

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-phenylbistrifluoromethane-sulfonimide; dimethylsulfide borane complex; 4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene; sulfuric acid; hexamethyldistannane; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; diethyl ether; toluene;

DOI:10.1016/0957-4166(95)00318-J

Reference yield:

Methyl 4-benzoylbutanoate (1501-04-8) → (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl (154859-09-3)

Guidance literature:

Multi-step reaction with 2 steps

1: (4S,5R)-4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene, BH₃*DMS / tetrahydrofuran; toluene / 1 h / Ambient temperature

2: 1.) LHMDS, DMPU, 2.) N-phenyltrifluoromethanesulfonimide, 3.) LiCl, Sn₂Me₆, Pd(PPh₃)4

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-phenylbistrifluoromethane-sulfonimide; dimethylsulfide borane complex; 4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene; hexamethyldistannane; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; toluene;

DOI:10.1016/0957-4166(95)00318-J

Reference yield:

(5R) methyl 5-hydroxy-5-phenylpentanoate (112022-82-9) → (6S,6'S)-6,6'-Diphenyl-5,6,5',6'-tetrahydro-4H,4'H-[2,2']bipyranyl (154859-09-3)

Guidance literature:

Multi-step reaction with 3 steps

1: camphorsulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

2: (4S,5R)-4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene, BH₃*DMS / tetrahydrofuran; toluene / 1 h / Ambient temperature

3: 1.) LHMDS, DMPU, 2.) N-phenyltrifluoromethanesulfonimide, 3.) LiCl, Sn₂Me₆, Pd(PPh₃)4

With 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone; tetrakis(triphenylphosphine) palladium⁽⁰⁾; N,N-phenylbistrifluoromethane-sulfonimide; dimethylsulfide borane complex; 4,5-diphenyl-2-methyl-3-oxa-1-aza-2-borolidene; camphor-10-sulfonic acid; hexamethyldistannane; lithium chloride; lithium hexamethyldisilazane; In tetrahydrofuran; dichloromethane; toluene;

DOI:10.1016/0957-4166(95)00318-J

upstream raw materials:

(6S) 6-phenyltetrahydro-2H-pyran-2-one

glutaric anhydride,

Methyl 4-benzoylbutanoate

phenylmagnesium bromide

Downstream raw materials:

(2'S,2''S,6'S,6''S) 1-O,6-O-(6,6'-diphenyl-3,3',4,4',5,5',6,6'-octahydro-2,2'-bi-2H-pyran-2,2'-diyl)-2-O,3-O,4-O,5-O-tetrabenzyl-D-myo-inositol

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-5-Benzyloxy-8-[(R)-2-(tert-butyl-diphenyl-silanyloxy)-1-methyl-ethyl]-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazole-2-sulfonyl)-1-methyl-ethyl]-5-benzyloxy-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one

(2S,6S,7S,9S,15R)-15-{(2S,5R,6R,8S)-8-[(S)-2-(Benzothiazol-2-ylsulfanyl)-1-methyl-ethyl]-5-benzyloxy-10-methyl-1,7-dioxa-spiro[5.5]undec-10-en-2-ylmethyl}-15-methyl-2,9-diphenyl-1,8,13,16-tetraoxa-dispiro[5.0.5.4]hexadecan-14-one