dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

Base Information

Chemical Name:dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester
CAS No.:228394-06-7
Molecular Formula:C₂₈H₃₆O₄S₂
Molecular Weight:500.723
Hs Code.:

dithiocarbonic acid <i>O</i>-(1,2-bis-benzyloxymethyl-4-<i>tert</i>-butoxy-bicyclo[3.1.0]hex-3-yl) ester <i>S</i>-methyl ester

Synonyms:dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

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Chemical Property of dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

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Technology Process of dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

There total 7 articles about dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester 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: 88.0%

: 75-15-0,12122-00-8
carbon disulfide

: 228393-99-5
(1S,2S,3R,4S,5S)-4-tert-butyloxy-1,2-di<(benzyloxy)methyl>-3-hydroxy-bicyclo<3.1.0>hexane

: 74-88-4
methyl iodide

: 228394-06-7
dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

Guidance literature:: With sodium hydride; In tetrahydrofuran; for 2h; Ambient temperature;
DOI:10.1021/jo990010m

Reference yield:

: 100-39-0
benzyl bromide

: 228394-06-7
dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

Guidance literature:: Multi-step reaction with 2 steps

1: 1.) (n-Bu₃Sn)2O, 2.) n-Bu₄NBr / 1.) toluene, reflux, 15 h, 2.) TolH, 105 deg C, 15 h

2: 88 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

With tetrabutylammomium bromide; sodium hydride; bis(tri-n-butyltin)oxide; In tetrahydrofuran;
DOI:10.1021/jo990010m

Reference yield:

: 156126-13-5
(1aR,1bR,4aS,5S,5aS)-1a-Benzyloxymethyl-3,3-dimethyl-hexahydro-2,4-dioxa-cyclopropa[a]pentalen-5-ol

: 228394-06-7
dithiocarbonic acid O-(1,2-bis-benzyloxymethyl-4-tert-butoxy-bicyclo[3.1.0]hex-3-yl) ester S-methyl ester

Guidance literature:: Multi-step reaction with 7 steps

1: 57 percent / p-TsOH*H₂O / 2 h / Heating

2: 100 percent / TPAP, NMO, 4A MS / CH₂Cl₂ / 0.67 h / Ambient temperature

3: 90 percent / n-BuLi / hexane; tetrahydrofuran / 0.5 h / 0 °C

4: 90 percent / BH₃*THF, NaBO₃*H₂O / tetrahydrofuran / 16 h / 0 - 20 °C

5: 87 percent / hexane; diethyl ether / 48 h / 70 °C

6: 1.) (n-Bu₃Sn)2O, 2.) n-Bu₄NBr / 1.) toluene, reflux, 15 h, 2.) TolH, 105 deg C, 15 h

7: 88 percent / NaH / tetrahydrofuran / 2 h / Ambient temperature

With sodium perborate; n-butyllithium; N-methyl-2-indolinone; tetrapropylammonium perruthennate; borane-THF; tetrabutylammomium bromide; sodium hydride; toluene-4-sulfonic acid; bis(tri-n-butyltin)oxide; In tetrahydrofuran; diethyl ether; hexane; dichloromethane;
DOI:10.1021/jo990010m