(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

Base Information

Chemical Name:(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane
CAS No.:175436-23-4
Molecular Formula:C₁₉H₃₀O₁₁
Molecular Weight:434.441
Hs Code.:

Synonyms:(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

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Chemical Property of (1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

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Technology Process of (1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

There total 5 articles about (1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane 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:

: 40653-32-5,641635-63-4
methyl 2,3,4-tri-O-benzyl-β-D-galactopyranoside

: 175436-23-4
(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

Guidance literature:: Multi-step reaction with 6 steps

1: 99 percent / pyridine / 2.5 h / Ambient temperature

2: 78 percent / 50percent NaH / dimethylformamide / 2 h / 100 °C

3: 1.) Hg(OAc)2, AcOH; NaCl, 2.) (i-Pr)2NEt / 1.) water, acetone, reflux, 1 h; reflux, 20 min, 2.) CH₃CN, reflux, 2 h

4: 78 percent / pyridine / toluene; tetrahydrofuran / -40 deg C, 0.5 h; -40 deg C to room temp., 1.5 h

5: 1.) 1 M BH₃*THF, 2.) 3 M NaOH, 30percent H₂O₂ / 1.) THF, 20 deg C, 17 h, 2.) THF, water, room temp., 5 h

6: 1.) H₂, 2.) pyridine / 1.) 5percent Pd/C / 1.) MeOH, 5 h, room temp.

With pyridine; sodium hydroxide; borane-THF; mercury(II) diacetate; hydrogen; dihydrogen peroxide; sodium hydride; acetic acid; N-ethyl-N,N-diisopropylamine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; N,N-dimethyl-formamide; toluene;
DOI:10.1139/v95-272

Reference yield:

: 175436-19-8
methyl 2,3,4-tri-O-benzyl-6-deoxy-α-L-arabino-hex-5-enopyranoside

: 175436-23-4
(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

Guidance literature:: Multi-step reaction with 4 steps

1: 1.) Hg(OAc)2, AcOH; NaCl, 2.) (i-Pr)2NEt / 1.) water, acetone, reflux, 1 h; reflux, 20 min, 2.) CH₃CN, reflux, 2 h

2: 78 percent / pyridine / toluene; tetrahydrofuran / -40 deg C, 0.5 h; -40 deg C to room temp., 1.5 h

3: 1.) 1 M BH₃*THF, 2.) 3 M NaOH, 30percent H₂O₂ / 1.) THF, 20 deg C, 17 h, 2.) THF, water, room temp., 5 h

4: 1.) H₂, 2.) pyridine / 1.) 5percent Pd/C / 1.) MeOH, 5 h, room temp.

With pyridine; sodium hydroxide; borane-THF; mercury(II) diacetate; hydrogen; dihydrogen peroxide; acetic acid; N-ethyl-N,N-diisopropylamine; sodium chloride; palladium on activated charcoal; In tetrahydrofuran; toluene;
DOI:10.1139/v95-272

Reference yield:

: 175436-20-1
(2R,3R,4S,5S)-2,3,4-Tris-benzyloxy-5-(2-methoxy-ethoxymethoxy)-cyclohexanone

: 175436-23-4
(1S)-1,2/3,4,5-2,3,4-triacetoxy-5-acetoxymethyl-1-methoxyethoxymethoxycyclohexane

Guidance literature:: Multi-step reaction with 3 steps

1: 78 percent / pyridine / toluene; tetrahydrofuran / -40 deg C, 0.5 h; -40 deg C to room temp., 1.5 h

2: 1.) 1 M BH₃*THF, 2.) 3 M NaOH, 30percent H₂O₂ / 1.) THF, 20 deg C, 17 h, 2.) THF, water, room temp., 5 h

3: 1.) H₂, 2.) pyridine / 1.) 5percent Pd/C / 1.) MeOH, 5 h, room temp.

With pyridine; sodium hydroxide; borane-THF; hydrogen; dihydrogen peroxide; palladium on activated charcoal; In tetrahydrofuran; toluene;
DOI:10.1139/v95-272