(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Base Information

Chemical Name:(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one
CAS No.:389807-38-9
Molecular Formula:C₃₁H₃₀INO₇
Molecular Weight:655.486
Hs Code.:

Synonyms:(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

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Chemical Property of (2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

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Technology Process of (2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

There total 12 articles about (2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-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:

: 75-47-8
iodoform

: (R)-(4-Methoxy-benzyloxy)-[(3aS,6S,6aR)-3a-(4-methoxy-benzyloxymethyl)-4-oxo-2-phenyl-3a,4,6,6a-tetrahydro-furo[3,4-d]oxazol-6-yl]-acetaldehyde

: 389807-38-9
(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Guidance literature:: With chromium dichloride; In tetrahydrofuran; at 0 - 25 ℃; for 5h;
DOI:10.1021/ja0118338

Reference yield:

: 101649-82-5
N-benzoyl-2-bromoglycine methyl ester

: 389807-38-9
(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Guidance literature:: Multi-step reaction with 13 steps

1.1: 61 percent / tetrahydrofuran / 3 h / -78 - 0 °C

2.1: 94 percent / LiOH / tetrahydrofuran; H₂O / 8 h / 25 °C

3.1: 97 percent / DCC / tetrahydrofuran / 12 h / 25 °C

4.1: NaH / tetrahydrofuran / 25 °C / Irradiation

4.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

4.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

5.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

6.1: 94 percent / aq. OsO₄; NMO / CH₂Cl₂ / 12 h / 25 °C

7.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C

8.1: 96 percent / (+)-camphorsulfonic acid / CH₂Cl₂ / 18 h / 25 °C

9.1: 98 percent / K₂CO₃ / methanol; diethyl ether / 0.5 h / 0 °C

10.1: 94 percent / trifluoromethanesulfonic anhydride; 4-DMAP; pyridine / 1,2-dichloro-ethane / 1 h / 83 °C

11.1: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

12.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

13.1: 49.8 mg / CrCl₂ / tetrahydrofuran / 5 h / 0 - 25 °C

With pyridine; chromium dichloride; peracetic acid; dmap; lithium hydroxide; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; (+)-10-camphorsulfonic acid; trifluoromethanesulfonic acid anhydride; dicyclohexyl-carbodiimide; sodium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; acetic acid; 1,2-dichloro-ethane; 7.1: modified Fleming oxidation / 13.1: Takai-Utimoto olefination;
DOI:10.1021/ja0118338

Reference yield:

: 389807-44-7
2-phenyl-4-(dimethylphenylsilyl)methyl-4,5-dihydro-5-oxazolone

: 389807-38-9
(2'E,1'S,6R,3aS,6aR)-6-[3'iodo-1'-(4-methoxybenzyloxy)prop-2'-en-1'-yl]-3a-(4-methoxybenzyloxymethyl)-2-phenyl-6,6a-dihydro-3aH-furo[3,4-d]oxazol-4-one

Guidance literature:: Multi-step reaction with 10 steps

1.1: NaH / tetrahydrofuran / 25 °C / Irradiation

1.2: (η³-C3H5PdCl)2; (R,R)-1,2-(o-PPh2-C6H4-CO-NH)2-cyclohexane / tetrahydrofuran / 25 °C

1.3: 68 percent / tetrahydrofuran / 3 h / 0 °C

2.1: 96 percent / (+)-camphorsulfonic acid / diethyl ether / 72 h / 25 °C

3.1: 94 percent / aq. OsO₄; NMO / CH₂Cl₂ / 12 h / 25 °C

4.1: 78 percent / peracetic acid; sodium bromide; sodium acetate / acetic acid / 2.5 h / 25 - 60 °C

5.1: 96 percent / (+)-camphorsulfonic acid / CH₂Cl₂ / 18 h / 25 °C

6.1: 98 percent / K₂CO₃ / methanol; diethyl ether / 0.5 h / 0 °C

7.1: 94 percent / trifluoromethanesulfonic anhydride; 4-DMAP; pyridine / 1,2-dichloro-ethane / 1 h / 83 °C

8.1: 97 percent / TBAF / tetrahydrofuran / 2 h / 25 °C

9.1: Dess-Martin periodinane; NaHCO₃ / CH₂Cl₂ / 1 h / 0 °C

10.1: 49.8 mg / CrCl₂ / tetrahydrofuran / 5 h / 0 - 25 °C

With pyridine; chromium dichloride; peracetic acid; dmap; osmium(VIII) oxide; N-methyl-2-indolinone; tetrabutyl ammonium fluoride; sodium acetate; sodium hydride; sodium hydrogencarbonate; potassium carbonate; Dess-Martin periodane; (+)-10-camphorsulfonic acid; trifluoromethanesulfonic acid anhydride; sodium bromide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; acetic acid; 1,2-dichloro-ethane; 4.1: modified Fleming oxidation / 10.1: Takai-Utimoto olefination;
DOI:10.1021/ja0118338