<1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol

Base Information

• Chemical Name: <1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol
• CAS No.: 159517-70-1
• Molecular Formula: C₂₄H₃₁N₃O₇
• Molecular Weight: 473.526

Synonyms:<1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol

Chemical Property of <1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol

Chemical Property:

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Technology Process of <1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol

There total 1 articles about <1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol 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: 62.0%

<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane (159517-69-8) → <1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol (159517-70-1)

Guidance literature:

With sodium azide; ammonium chloride; In ethylene glycol; N,N-dimethyl-formamide; at 125 ℃; for 48h;

DOI:10.7164/antibiotics.47.932

Reference yield: 72.0%

<1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol (159517-70-1) → (1R,2R,3S,4R,5R)-2-Amino-5-benzyloxy-1-benzyloxymethyl-3,4-bis-methoxymethoxy-cyclopentanol (161105-77-7)

Guidance literature:

With lithium aluminium tetrahydride; In diethyl ether; at 0 ℃; for 3h;

DOI:10.7164/antibiotics.47.932

Reference yield:

<1R-(1α,2α,3α,4β,5β)>-5-Azido-2-benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-1-cyclopentanol (159517-70-1) → (1R,2S,3R,4R,5R)-3-Amino-5-benzyloxy-4-benzyloxymethyl-cyclopentane-1,2,4-triol

Guidance literature:

Multi-step reaction with 2 steps

1: 72 percent / LiAlH₄ / diethyl ether / 3 h / 0 °C

2: 10percent HCl / methanol / 1.) 0 deg C, 5 min, 2.) 60 deg C, 7 h

With hydrogenchloride; lithium aluminium tetrahydride; In methanol; diethyl ether;

DOI:10.7164/antibiotics.47.932

upstream raw materials:

<1R-(1α,2β,3β,4α,5α)>-2-Benzyloxy-1-benzyloxymethyl-3,4-di(methoxymethoxy)-6-oxabicyclo<3.1.0>hexane

Downstream raw materials:

(1R,2R,3S,4R,5R)-2-Amino-5-benzyloxy-1-benzyloxymethyl-3,4-bis-methoxymethoxy-cyclopentanol

N-(2,3,4,6-Tetra-O-benzyl-1-deoxy-α-D-glucopyranosyl)-N'-<<1R-(1α,2α,3α,4β,5β)>-2-benzyloxy-1-benzyloxymethyl-1,3,4-trihydroxycyclopentan-5-yl>thiourea

<<3aR-(3aα,4α,5α,6α,6aα)>-N-(5-Benzyloxy-4-benzyloxymethyl-4,6-dihydroxy-3a,5,6,6a-tetrahydro-4H-cyclopentoxazol-2-yl)>-2,3,4,6-tetra-O-benzyl-α-D-glucopyranosylamine

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