(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

Base Information

Chemical Name:(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal
CAS No.:105539-47-7
Molecular Formula:C₂₀H₃₂O₃S₂
Molecular Weight:384.604
Hs Code.:

Synonyms:(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

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Chemical Property of (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

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Technology Process of (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

There total 8 articles about (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal 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: 84.0%

: 109-80-8
1.3-propanedithiol

: 105616-10-2
methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptopyranoside

: 105539-47-7
(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

Guidance literature:: With boron trifluoride diethyl etherate; In dichloromethane; at -78 - 0 ℃;
DOI:10.1021/ja00237a037

Reference yield:

: 72486-93-2
1-methoxy-2-methyl-3-trimethylsiloxy-1,3-pentadiene

: 105539-47-7
(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

Guidance literature:: Multi-step reaction with 7 steps

1: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 30 min

2: 91 percent / LiAlH₄ / diethyl ether / -78 °C

3: 92 percent / p-TsOH*H₂O / 10 h / Ambient temperature

4: 1) BF₃*THF, 2) 30percent H₂O₂, NaOH / 1) THF, 0 deg C, 30 min, 2) THF, 12 h, RT

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C to RT

6: 86 percent / NaBH₄ / methanol / 0.33 h / -25 °C

7: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 0 °C

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; boron trifluoride diethyl etherate; dihydrogen peroxide; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja00237a037

Reference yield:

: 74130-31-7,79026-61-2,79027-28-4,73814-73-0
3-(benzyloxy)-2-methylpropanal

: 105539-47-7
(+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptose cyclic 1,3-propanediyl mercaptal

Guidance literature:: Multi-step reaction with 7 steps

1: 1) TiCl₄ / 1) CH₂Cl₂, -78 deg C, 5 min, 2) CH₂Cl₂, -78 deg C, 30 min

2: 91 percent / LiAlH₄ / diethyl ether / -78 °C

3: 92 percent / p-TsOH*H₂O / 10 h / Ambient temperature

4: 1) BF₃*THF, 2) 30percent H₂O₂, NaOH / 1) THF, 0 deg C, 30 min, 2) THF, 12 h, RT

5: 1) (COCl)2, DMSO, 2) Et₃N / 1) CH₂Cl₂, -78 deg C, 10 min, 2) CH₂Cl₂, -78 deg C to RT

6: 86 percent / NaBH₄ / methanol / 0.33 h / -25 °C

7: 84 percent / BF₃*Et₂O / CH₂Cl₂ / -78 - 0 °C

With sodium hydroxide; sodium tetrahydroborate; lithium aluminium tetrahydride; oxalyl dichloride; boron trifluoride-tetrahydrofuran complex; boron trifluoride diethyl etherate; dihydrogen peroxide; titanium tetrachloride; toluene-4-sulfonic acid; dimethyl sulfoxide; triethylamine; In methanol; diethyl ether; dichloromethane;
DOI:10.1021/ja00237a037