(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

Base Information

Chemical Name:(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol
CAS No.:499121-00-5
Molecular Formula:C₂₁H₂₆O₅
Molecular Weight:358.434
Hs Code.:

Synonyms:(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

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Business phase:: The product has achieved commercial mass production^*data from LookChem market partment

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Chemical Property of (3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

Chemical Property:

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Technology Process of (3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

There total 13 articles about (3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol 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:

: (4R,5S)-4-((R)-1-Benzyloxy-propyl)-5-((R)-1-hydroxy-2-phenyl-ethyl)-2,2-dimethyl-[1,3]dioxolane-4-carbaldehyde

: 499121-00-5
(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

Guidance literature:: With trifluoroacetic acid; at 20 ℃; for 9h;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 64638-65-9
5,6-dideoxy-1,2-O-isopropylidene-α-D-erythro-hexofuranos-3-ulose

: 499121-00-5
(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

Guidance literature:: Multi-step reaction with 12 steps

1.1: tetrahydrofuran / 1 h / -18 °C

2.1: aq. AcOH / 11 h / 80 °C

3.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

4.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

5.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

6.1: DMAP; pyridine / 4 h / Heating

7.1: NaH / dimethylformamide / 8 h / 20 °C

8.1: 6.59 g / CSA / methanol / 48 h / 20 °C

9.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

10.1: 14 percent / tetrahydrofuran / 20 °C

11.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

11.2: Ph₃P / CH₂Cl₂ / 1.5 h / -78 - 20 °C

12.1: aq. CF₃CO₂H / 9 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; ozone; acetic acid; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 9.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703

Reference yield:

: 16749-42-1
5,6-dideoxy-1,2-O-isopropylidene-α-D-xylo-hexofuranose

: 499121-00-5
(3S,4S,5R)-5-Benzyl-3-((R)-1-benzyloxy-propyl)-tetrahydro-furan-2,3,4-triol

Guidance literature:: Multi-step reaction with 13 steps

1.1: pyridinium chlorochromate; molecular sieves 4 Angstroem / CH₂Cl₂ / 10 h / 20 °C

2.1: tetrahydrofuran / 1 h / -18 °C

3.1: aq. AcOH / 11 h / 80 °C

4.1: 5.60 g / N-iodosuccinimide; n-Bu₄NI / CH₂Cl₂ / 20 h / 20 °C

5.1: 79 percent / CSA / acetone / 6 h / 40 °C / 225.02 Torr

6.1: 91 percent / LiAlH₄ / tetrahydrofuran / 2 h / 0 °C

7.1: DMAP; pyridine / 4 h / Heating

8.1: NaH / dimethylformamide / 8 h / 20 °C

9.1: 6.59 g / CSA / methanol / 48 h / 20 °C

10.1: 96 percent / Dess-Martin periodinane / CH₂Cl₂ / 3 h / 20 °C

11.1: 14 percent / tetrahydrofuran / 20 °C

12.1: O₃ / CH₂Cl₂ / 1 h / -78 °C

12.2: Ph₃P / CH₂Cl₂ / 1.5 h / -78 - 20 °C

13.1: aq. CF₃CO₂H / 9 h / 20 °C

With pyridine; dmap; N-iodo-succinimide; lithium aluminium tetrahydride; 4 A molecular sieve; camphor-10-sulfonic acid; tetra-(n-butyl)ammonium iodide; sodium hydride; Dess-Martin periodane; ozone; acetic acid; pyridinium chlorochromate; trifluoroacetic acid; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; 10.1: Dess-Martin oxidation;
DOI:10.1246/bcsj.77.1703