(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

Base Information

Chemical Name:(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane
CAS No.:828935-15-5
Molecular Formula:C₂₄H₂₈O₄
Molecular Weight:380.484
Hs Code.:

Synonyms:(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

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Chemical Property of (1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

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Technology Process of (1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

There total 10 articles about (1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane 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: 99.0%

: 100-39-0
benzyl bromide

: 828935-14-4,389626-30-6
(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-(hydroxymethyl)bicyclo[3.1.0]hexan-2-ol

: 828935-15-5
(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

Guidance literature:: With sodium hydride;
DOI:10.1081/NCN-120021954

Reference yield:

: 495397-65-4
ethyl (1S,3S,4S,5S)-3,4-isopropylenedioxy-2-oxobicyclo[3.1.0]hexane-1-carboxylate

: 828935-15-5
(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 2 steps

1: 55 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

2: 62 percent / NaH / dimethylformamide / 3 h / 75 °C

With sodium hydride; diisobutylaluminium hydride; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1021/jo0487606

Reference yield:

: 25581-41-3
D-erythronolactone acetonide

: 828935-15-5
(1S,2R,3S,4S,5S)-3,4-O-isopropylidene-1-[(phenylmethoxy)methyl]-2-(phenylmethoxy)bicyclo[3.1.0]hexane

Guidance literature:: Multi-step reaction with 10 steps

1: 90 percent / DIBAL-H / CH₂Cl₂ / -78 °C

2: 60 percent / t-BuOK / tetrahydrofuran / 0 - 20 °C

3: (COCl)2; DMSO; Et₃N / CH₂Cl₂ / -78 - 20 °C

4: NaOCl

5: tetrahydrofuran / 0 - 30 °C

6: 0.293 g / tetrahydrofuran / -78 °C

7: 70 percent / Et₃N / acetonitrile / 0.5 h / 20 °C

8: 36 percent / CuI / toluene / 8 h / Heating

9: 55 percent / DIBAL-H / toluene; tetrahydrofuran / 1 h / -78 °C

10: 62 percent / NaH / dimethylformamide / 3 h / 75 °C

With sodium hypochlorite; copper(l) iodide; oxalyl dichloride; potassium tert-butylate; sodium hydride; diisobutylaluminium hydride; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; toluene; acetonitrile; 3: Swern oxidation / 6: Dieckmann condensation;
DOI:10.1021/jo0487606