(3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid

Base Information

• Chemical Name: (3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid
• CAS No.: 86535-49-1
• Molecular Formula: C₁₆H₂₀O₆
• Molecular Weight: 308.331

Synonyms:(3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid

Chemical Property of (3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid

Chemical Property:

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Technology Process of (3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid

There total 1 articles about (3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid 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: 87.0%

3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribopentodialdo-1,4-furanose (81841-44-3) → (3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid (86535-49-1)

Guidance literature:

With jones reagent; In acetone; at 0 ℃;

DOI:10.1016/S0040-4039(00)86396-0

Reference yield:

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid (86535-49-1) → (2S,3S)-3-Benzyloxy-2-hydroxy-4-[(E)-hydroxyimino]-3-methyl-butyric acid ethyl ester (86535-52-6)

Guidance literature:

Multi-step reaction with 4 steps

1: HCl / Ambient temperature

2: aq. acetic acid / Heating

3: NaIO₄ / H₂O; methanol / 0 °C

4: hydroxylamine hydrochloride / pyridine / Ambient temperature

With sodium periodate; hydroxylamine hydrochloride; hydrogenchloride; In pyridine; methanol; water; acetic acid;

DOI:10.1016/S0040-4039(00)86396-0

Reference yield:

(3aR,5S,6S,6aR)-6-Benzyloxy-2,2,6-trimethyl-tetrahydro-furo[2,3-d][1,3]dioxole-5-carboxylic acid (86535-49-1) → (2S,3S)-4-Amino-3-cyclohexylmethoxy-2-hydroxy-3-methyl-butyric acid ethyl ester

Guidance literature:

Multi-step reaction with 5 steps

1: HCl / Ambient temperature

2: aq. acetic acid / Heating

3: NaIO₄ / H₂O; methanol / 0 °C

4: hydroxylamine hydrochloride / pyridine / Ambient temperature

5: hydrogen / PtO₂ / acetic acid

With sodium periodate; hydroxylamine hydrochloride; hydrogen; hydrogenchloride; platinum(IV) oxide; In pyridine; methanol; water; acetic acid;

DOI:10.1016/S0040-4039(00)86396-0

upstream raw materials:

3-O-benzyl-1,2-O-isopropylidene-3-C-methyl-α-D-ribopentodialdo-1,4-furanose

Downstream raw materials:

(2S,3S)-3-Benzyloxy-2-hydroxy-4-[(E)-hydroxyimino]-3-methyl-butyric acid ethyl ester

(2S,3R)-3-Benzyloxy-2-formyloxy-3-methyl-4-oxo-butyric acid ethyl ester

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