(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

Base Information

Chemical Name:(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane
CAS No.:106502-63-0
Molecular Formula:C₃₀H₄₂O₁₀S₂
Molecular Weight:626.789
Hs Code.:

Synonyms:(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

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Chemical Property of (Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

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Technology Process of (Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

There total 7 articles about (Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane 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: 91.0%

: 106470-28-4
(1S,3R,4S,5R)-4-Methoxymethoxy-5-((Z)-7-methoxymethoxy-hept-2-enyl)-cyclopentane-1,3-diol

: 98-59-9
p-toluenesulfonyl chloride

: 106502-63-0
(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

Guidance literature:: With pyridine; at 0 ℃; for 96h;
DOI:10.1021/jo00381a027

Reference yield:

: 20476-33-9
1α,4α-dibenzyloxy-2α,3α-epoxycyclopentane

: 106502-63-0
(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 7 steps

1: 98.6 percent / diethyl ether / 1.) -78 deg C, 1.5 h, 2.) from -78 deg C to -30 deg C, 2 h

2: 1.) O₃, 2.) dimethyl sulfide / 1.) CH₂Cl₂, methanol, -78 deg C, 2.) CH₂Cl₂, methanol, from -78 deg C to 22 deg C, 3.5 h

3: 1.) NaH, DMSO / 1.) 5 min, 2.) 22 deg C, 1.5 h

4: 68 percent / LiAlH₄ / diethyl ether / 18 h / 22 °C

5: 100 percent / diethylaniline / CH₂Cl₂ / 48 h / 22 °C

6: 99 percent / Na, NH₃, ethanol / tetrahydrofuran / 1.5 h

7: 91 percent / pyridine / 96 h / 0 °C

With pyridine; lithium aluminium tetrahydride; dimethylsulfide; ethanol; ammonia; sodium; sodium hydride; ozone; dimethyl sulfoxide; N,N-diethylaniline; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00381a027

Reference yield:

: 37619-52-6,37619-64-0,81768-39-0,106565-04-2
(1RS,2RS,3RS,5SR)-3,5-bis(phenylmethoxy)-2-(2-propenyl)-1-cyclopentanol

: 106502-63-0
(Z)-(1SR,2RS,3RS,4RS)-2-(2-oxapropyloxy)-3-(8,10-dioxa-2-undecenyl)-1,4-bis<(p-toluenesulfonyl)oxy>cyclopentane

Guidance literature:: Multi-step reaction with 6 steps

1: 1.) O₃, 2.) dimethyl sulfide / 1.) CH₂Cl₂, methanol, -78 deg C, 2.) CH₂Cl₂, methanol, from -78 deg C to 22 deg C, 3.5 h

2: 1.) NaH, DMSO / 1.) 5 min, 2.) 22 deg C, 1.5 h

3: 68 percent / LiAlH₄ / diethyl ether / 18 h / 22 °C

4: 100 percent / diethylaniline / CH₂Cl₂ / 48 h / 22 °C

5: 99 percent / Na, NH₃, ethanol / tetrahydrofuran / 1.5 h

6: 91 percent / pyridine / 96 h / 0 °C

With pyridine; lithium aluminium tetrahydride; dimethylsulfide; ethanol; ammonia; sodium; sodium hydride; ozone; dimethyl sulfoxide; N,N-diethylaniline; In tetrahydrofuran; diethyl ether; dichloromethane;
DOI:10.1021/jo00381a027