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You can start on any corner. For the chair conformation in particular, there will always be one corner pointing up and one corner pointing down. On the corner pointing up draw an axial up bond and on the corner pointing down draw an axial down bond. From there, just alternate axial up/down on each successive Carbon. Then draw the equatorials on the axials. If there is an axial up, draw an equatorial down and vice versa.
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