2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Base Information

Chemical Name:2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran
CAS No.:96150-91-3
Molecular Formula:C₂₈H₄₂O₇Si
Molecular Weight:518.723
Hs Code.:

2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Synonyms:2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

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Chemical Property of 2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

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Technology Process of 2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

There total 13 articles about 2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran 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: 95.0%

: 1779-49-3
Methyltriphenylphosphonium bromide

: 2(S)-formyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

: 96150-91-3
2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: With n-butyllithium; In tetrahydrofuran; hexane; for 10h; Ambient temperature;
DOI:10.1021/ja00297a038

Reference yield:

: 87-72-9,608-45-7,608-46-8,608-47-9,2460-44-8,6748-95-4,6763-34-4,7261-26-9,7283-06-9,7283-07-0,7296-55-1,7296-56-2,7296-58-4,7296-59-5,7296-60-8,7296-61-9,7296-62-0,7322-30-7,10257-31-5,10257-32-6,10257-33-7,10257-34-8,10257-35-9,19982-83-3,20242-88-0,28697-53-2,36562-42-2,41546-41-2,89299-64-9,107655-34-5,115794-06-4,115794-07-5,130550-15-1,130606-21-2
D-Xylose

: 96150-91-3
2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 10 steps

1: 1.) pyridinium p-toluenesulfonate; 2.) copper sulfate / 1.) 75 deg C, 48 h; 2.) 30 h, room temp.

2: 1.) (COCl)2, Me₂SO, Et₃N / 1.) THF, -40 deg C, 5 min; 2.) Et₂O, 2 h, -78 deg C

3: 100 percent / p-TsOH*H₂O, CuSO₄ / 36 h / Ambient temperature

4: t-BuOK / dimethylsulfoxide / 0.17 h / 80 °C

5: 1.) (i-Pr)2NEt; 2.) Hg(OAc)2 / 1.) CH₂Cl₂, 24 h, room temp.; 2.) THF, H₂O, 20 min, room temp.

6: 1.) P(NMe₂)3; 2.) Li, NH₃ / 1.) CCl₄, THF, 25 min, -78 deg C; 2.) -78 deg C, 35 min

8: 96 percent / LAH / diethyl ether / 1 h / 0 °C

9: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂ / 20 h / -78 °C

10: 95 percent / n-BuLi / hexane; tetrahydrofuran / 10 h / Ambient temperature

With lithium aluminium tetrahydride; n-butyllithium; copper(I) sulfate; oxalyl dichloride; potassium tert-butylate; mercury(II) diacetate; ammonia; pyridinium p-toluenesulfonate; lithium; toluene-4-sulfonic acid; copper(II) sulfate; dimethyl sulfoxide; triethylamine; N-ethyl-N,N-diisopropylamine; Hexamethylphosphorous triamide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; dimethyl sulfoxide;
DOI:10.1021/ja00297a038

Reference yield:

: 74912-02-0,79940-48-0,94118-99-7,20689-03-6
1-O-benzyl-2,3-O-isopropylidene-α-D-manno-furanose

: 96150-91-3
2(R)-vinyl-2-<2,5-dihydro-5(S)-(<2-(trimethylsilyl)ethoxymethoxy>methyl)-3-methyl-2(R)-furyl>-3(R),4(S)-(dimethylmethylenedioxy)-5(S)-(benzyloxy)tetrahydrofuran

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) NaIO₄; 2.) AgNO₃, KOH (85percent) / 1.) MeOH, H₂O, 1 h 75 min; 2.) H₂O, EtOH, 9.5 h

2: 4.10 g / (COCl)2, DMF / benzene / 2 h / Ambient temperature

4: 96 percent / LAH / diethyl ether / 1 h / 0 °C

5: (COCl)2, Me₂SO, Et₃N / CH₂Cl₂ / 20 h / -78 °C

6: 95 percent / n-BuLi / hexane; tetrahydrofuran / 10 h / Ambient temperature

With potassium hydroxide; sodium periodate; lithium aluminium tetrahydride; n-butyllithium; oxalyl dichloride; silver nitrate; dimethyl sulfoxide; triethylamine; N,N-dimethyl-formamide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane; benzene;
DOI:10.1021/ja00297a038