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

Base Information

Chemical Name:methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptopyranoside
CAS No.:105616-10-2
Molecular Formula:C₁₈H₂₈O₄
Molecular Weight:308.418
Hs Code.:

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

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Chemical Property of methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptopyranoside

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Technology Process of methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptopyranoside

There total 7 articles about methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-talo-heptopyranoside 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: 6.0%

: 105539-46-6
(2R,3S,5R,6S)-2-((R)-2-Benzyloxy-1-methyl-ethyl)-6-methoxy-3,5-dimethyl-tetrahydro-pyran-4-one

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

: 105539-45-5
methyl (+/-)-2,4,6-trideoxy-2,4,6-trimethyl-7-O-(phenylmethyl)-D-glycero-α-D-ido-heptopyranoside

Guidance literature:: With sodium tetrahydroborate; In methanol; at -25 ℃; for 0.333333h;
DOI:10.1021/ja00237a037

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 6 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

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